5-Benzyloxyindole

Off-white to beige powder

Following a procedure similar to Example 32, 4-benzyloxy-2-(2-pyrrolidinylvinyl)nitrobenzene as a starting material was reduced in the presence of 5 percent rhodium/carbon powder and as a metal compound, ferrous(II) acetate, nickel(II) nitrate or cobalt(III) acetylacetonate as the catalyst of the present invention. The results are shown in the following Table 5, and in the case where the reducing agent of the present invention was used, 5-benzyloxyindole was obtained in a higher yield and 5-hydroxyindole was byproduced in a lower yield, compared to Comparison Example 4.Following a procedure similar to Example 32, 4-benzyloxy-2-(2-pyrrolidinylvinyl)nitrobenzene as a starting material was reduced in the presence of 5 percent rhodium/carbon powder and as a metal compound, ferrous(II) acetate, nickel(II) nitrate or cobalt(III) acetylacetonate as the catalyst of the present invention. The results are shown in the following Table 5, and in the case where the reducing agent of the present invention was used, 5-benzyloxyindole was obtained in a higher yield and 5-hydroxyindole was byproduced in a lower yield, compared to Comparison Example 4.Following a procedure similar to Example 32, 4-benzyloxy-2-(2-pyrrolidinylvinyl)nitrobenzene as a starting material was reduced in the presence of 5 percent rhodium/carbon powder and as a metal compound, ferrous(II) acetate, nickel(II) nitrate or cobalt(III) acetylacetonate as the catalyst of the present invention. The results are shown in the following Table 5, and in the case where the reducing agent of the present invention was used, 5-benzyloxyindole was obtained in a higher yield and 5-hydroxyindole was byproduced in a lower yield, compared to Comparison Example 4.Following a procedure similar to Example 32, 4-benzyloxy-2-(2-pyrrolidinylvinyl)nitrobenzene as a starting material was reduced in the presence of 5 percent rhodium/carbon powder and as a metal compound, ferrous(II) acetate, nickel(II) nitrate or cobalt(III) acetylacetonate as the catalyst of the present invention. The results are shown in the following Table 5, and in the case where the reducing agent of the present invention was used, 5-benzyloxyindole was obtained in a higher yield and 5-hydroxyindole was byproduced in a lower yield, compared to Comparison Example 4.0.5 g (3.8 mmol) 5-hydroxyindole (1 ) were dissolved in 5 ml acetone and mixed with 535 μΙ (4.5 mmol) benzylbromide (BnBr), 2.45 g (7.5 mmol) CsBenzylbromide (2.0 mL, 16.8 mmol) and K2CO3 (3.1 g, 22.5 mmol) were added to a solution of 5-hydroxyindole 1 (2.0 g, 15.0 mmol) in DMF (10 mL) and the mixture was stirred and heated at reflux. After 24 h, the mixture was cooled to r.t. and the reaction was quenched with 10percent aq HCl. The mixture was extracted with EtOAc (3 50 mL), MgSO4. The solvent was removed and the residue was purified by silica gel column chromatography (EtOAc/hexane, 1:6) to give 2. Yield: 3 g (91percent); colorless solid; mp 97-100 °C (CHCl3). IR (CHCl3): 3483, 1626, 1581, 1477, 1452, 1281, 1153 cm-1. 1H NMR (500 MHz, CDCl3): δ = 8.03 (br. s, 1H), 7.52 (d, J = 7.5 Hz, 2 H), 7.43 (t, J = 7.5 Hz, 2 H), 7.36 (t, J = 7.5 Hz, 1H), 7.27 (d, J = 8.6 Hz, 1H), 7.24 (d, J = 2.3 Hz, 1H), 7.15 (t, J = 2.8 Hz, 1H), 6.99 (dd, J = 8.6, 2.3 Hz, 1H), 6.51 (t, J = 2.3 Hz, 1H), 5.15 (s, 2 H). 13C NMR (125 MHz, CDCl3): δ = 153.5, 137.8, 131.3, 128.7, 128.4, 127.9, 127.7, 125.1, 113.2, 111.9, 104.1, 102.5, 71.1. HRMS (EI): m/z [M+] calcd for C15H13NO: 223.0997; found: 223.1028.A mixture ofof5-hydroxyindole 1 (750 mg, 5.63 mmol), benzyl bromide (1.05 g, 6.19 mmol), K2C03 (2.30 g, 16.89 mmol) and DMF (10 mL), was stirred at RT for 16 h. The mixture was partitioned between water (100 mL) and EtOAc (50 mL). The organic layer was separated and the aq. layer re-extracted with additional EtOAc (50 mL). The combined organic layers were dried over Na2SO4, filtered, and the filtrate concentrated under reduced pressure. The residue was purified (silica gel; eluting with 0-100percent EtOAc in hexanes), to afford compound 2 (1.12 g, 88percent) as a light yellow solid. LCMS Mass: 224.0 (M+1).Compound 6 was prepared according to a previously described procedure

Reactant in regio- and stereoselective morpholine-catalyzed direct C-3 alkenylation with α,β-unsaturated aldehydes Reactant in selective debenzylation of protective groups using SiliaCat-palladium under mild reaction conditions Reactant in metal-free Friedel-Crafts alkylation reactions Reactant in preparation of protein kinase (PKC) inhibitors Reactant in preparation of indole/quinoline carbothioic acid amide derivatives.

Molecular Weight:223.27
XLogP3:3.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:3
Exact Mass:223.099714038
Monoisotopic Mass:223.099714038
Topological Polar Surface Area:25
Heavy Atom Count:17
Complexity:237
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes