2-broMo-5-cyclopropylpyridine

General procedure: Aminopyridine (1 mmol) and corresponding Cu(II) halide (0.5 mmol) were dissolveddibromo(chloro)methane (6 mL) at 25 °C under an argon atmosphere. Alkyl nitrite (1.1 mmol)was added dropwise over 5 min and reaction mixture stirred at the appropriate temperature(Table 1 and 2) until GC-MS analysis of the reaction mixture indicated full consumption the of starting material. The reaction mixture was poured into 1 N NaOH (20 mL), stirred for 1 h andextracted with CH2Cl2 (3 × 20 mL). The combined organic extracts were dried (Na2SO4) andevaporated to dryness. The crude product was purified by column chromatography on silica gel, eluting with CH2Cl2. 2-Bromo-5-cyclopropylpyridine (2a): yield 76percent. Rf = 0.49. 1H NMR (400MHz, CDCl3) δ 8.17 (d, J = 2.4 Hz, 1H), 7.34 (d, J = 8.2 Hz, 1H), 7.15 (dd, J =8.2, 2.4 Hz, 1H), 1.89 – 1.82 (m, 1H), 1.10 – 0.98 (m, 2H), 0.75 – 0.64 (m, 2H). 13C NMR (100 MHz, CDCl3) δ 148.6, 138.8, 138.7, 135.4, 127.5, 12.5, 9.1. GC-MS: tR= 7.031 min (m/z (rel. in.)) 197 (43.52percent), 199 (41.85percent).General procedure: Aminopyridine (1 mmol) and corresponding Cu(II) halide (0.5 mmol) were dissolved dibromo(chloro)methane (6 mL) at 25 °C under an argon atmosphere. Alkyl nitrite (1.1 mmol)was added dropwise over 5 min and reaction mixture stirred at the appropriate temperature(Table 1 and 2) until GC-MS analysis of the reaction mixture indicated full consumption the of starting material. The reaction mixture was poured into 1 N NaOH (20 mL), stirred for 1 h and extracted with CH2Cl2 (3 × 20 mL). The combined organic extracts were dried (Na2SO4) andevaporated to dryness. The crude product was purified by column chromatography on silica gel, eluting with CH2Cl2.General procedure: Aminopyridine (1 mmol) and corresponding Cu(II) halide (0.5 mmol) were dissolved dibromo(chloro)methane (6 mL) at 25 °C under an argon atmosphere. Alkyl nitrite (1.1 mmol)was added dropwise over 5 min and reaction mixture stirred at the appropriate temperature(Table 1 and 2) until GC-MS analysis of the reaction mixture indicated full consumption the of starting material. The reaction mixture was poured into 1 N NaOH (20 mL), stirred for 1 h and extracted with CH2Cl2 (3 × 20 mL). The combined organic extracts were dried (Na2SO4) andevaporated to dryness. The crude product was purified by column chromatography on silica gel, eluting with CH2Cl2.General procedure: Aminopyridine (1 mmol) and corresponding Cu(II) halide (0.5 mmol) were dissolved dibromo(chloro)methane (6 mL) at 25 °C under an argon atmosphere. Alkyl nitrite (1.1 mmol)was added dropwise over 5 min and reaction mixture stirred at the appropriate temperature(Table 1 and 2) until GC-MS analysis of the reaction mixture indicated full consumption the of starting material. The reaction mixture was poured into 1 N NaOH (20 mL), stirred for 1 h and extracted with CH2Cl2 (3 × 20 mL). The combined organic extracts were dried (Na2SO4) andevaporated to dryness. The crude product was purified by column chromatography on silica gel, eluting with CH2Cl2.General procedure: Aminopyridine (1 mmol) and corresponding Cu(II) halide (0.5 mmol) were dissolveddibromo(chloro)methane (6 mL) at 25 °C under an argon atmosphere. Alkyl nitrite (1.1 mmol)was added dropwise over 5 min and reaction mixture stirred at the appropriate temperature(Table 1 and 2) until GC-MS analysis of the reaction mixture indicated full consumption the of starting material. The reaction mixture was poured into 1 N NaOH (20 mL), stirred for 1 h andextracted with CH2Cl2 (3 × 20 mL). The combined organic extracts were dried (Na2SO4) andevaporated to dryness. The crude product was purified by column chromatography on silica gel, eluting with CH2Cl2. 2-Bromo-5-cyclopropylpyridine (2a): yield 76percent. Rf = 0.49. 1H NMR (400MHz, CDCl3) δ 8.17 (d, J = 2.4 Hz, 1H), 7.34 (d, J = 8.2 Hz, 1H), 7.15 (dd, J =8.2, 2.4 Hz, 1H), 1.89 – 1.82 (m, 1H), 1.10 – 0.98 (m, 2H), 0.75 – 0.64 (m, 2H). 13C NMR (100 MHz, CDCl3) δ 148.6, 138.8, 138.7, 135.4, 127.5, 12.5, 9.1. GC-MS: tR= 7.031 min (m/z (rel. in.)) 197 (43.52percent), 199 (41.85percent).General procedure: Aminopyridine (1 mmol) and corresponding Cu(II) halide (0.5 mmol) were dissolveddibromo(chloro)methane (6 mL) at 25 °C under an argon atmosphere. Alkyl nitrite (1.1 mmol)was added dropwise over 5 min and reaction mixture stirred at the appropriate temperature(Table 1 and 2) until GC-MS analysis of the reaction mixture indicated full consumption the of starting material. The reaction mixture was poured into 1 N NaOH (20 mL), stirred for 1 h andextracted with CH2Cl2 (3 × 20 mL). The combined organic extracts were dried (Na2SO4) andevaporated to dryness. The crude product was purified by column chromatography on silica gel, eluting with CH2Cl2.General procedure: Aminopyridine (1 mmol) and corresponding Cu(II) halide (0.5 mmol) were dissolveddibromo(chloro)methane (6 mL) at 25 °C under an argon atmosphere. Alkyl nitrite (1.1 mmol)was added dropwise over 5 min and reaction mixture stirred at the appropriate temperature(Table 1 and 2) until GC-MS analysis of the reaction mixture indicated full consumption the of starting material. The reaction mixture was poured into 1 N NaOH (20 mL), stirred for 1 h andextracted with CH2Cl2 (3 × 20 mL). The combined organic extracts were dried (Na2SO4) andevaporated to dryness. The crude product was purified by column chromatography on silica gel, eluting with CH2Cl2. 2-Bromo-5-cyclopropylpyridine (2a): yield 76percent. Rf = 0.49. 1H NMR (400MHz, CDCl3) δ 8.17 (d, J = 2.4 Hz, 1H), 7.34 (d, J = 8.2 Hz, 1H), 7.15 (dd, J =8.2, 2.4 Hz, 1H), 1.89 – 1.82 (m, 1H), 1.10 – 0.98 (m, 2H), 0.75 – 0.64 (m, 2H). 13C NMR (100 MHz, CDCl3) δ 148.6, 138.8, 138.7, 135.4, 127.5, 12.5, 9.1. GC-MS: tR= 7.031 min (m/z (rel. in.)) 197 (43.52percent), 199 (41.85percent).

Molecular Weight:198.06
XLogP3:2.8
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:196.98401
Monoisotopic Mass:196.98401
Topological Polar Surface Area:12.9
Heavy Atom Count:10
Complexity:122
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes