(6-BROMO-1H-INDOL-2-YL)METHANOL

White to light yellow powder or solid

To a solution of 6-bromo-1H-indole-2-carboxylic acid (1.00 g, 4.20 mmol) in THF (20.0 mL) was added LiAlHMethyl 6-bromo-1H-indole-2-carboxylate (200 mg, 0.79 mmol) and lithium borohydride (86 mg, 3.95 mmol) were dissolved in anhydrous tetrahydrofuran (10 mL) at 0 C, and it was stirred for overnight at room temperature. The reaction mixture was diluted with ethyl acetate, and it was washed with saturated NH4Cl and brine. The organic layer was dried over Na2S04, and it was concentrated under reduced pressure. The residue was purified on an ISCO chromatograph (0-50% ethyl acetate/hexane) to give product as a white solid (162 mg, 91 %); NMR (300 MHz) (CDCh) d 8.42 (bs, 1H), 7.47 (s, 1H), 7.42 (d, j= 8 Hz, 1H), 7.20 (dd, j = 10 Hz, J= 2 Hz, 1H), 6.36 (d, J= 1 Hz, 1H), 4.80 (s, 2H).Compound TDI01155-1 (600 mg, 2.36 mmol) was dissolved in tetrahydrofuran (20 mL), LiAlH4 (269.3 mg, 7.09mmol) was slowly added at 0C, the reaction was slowly warmed to room temperature after being stirred for 30 minutes, and was further stirred at room temperature for 5 h. LC-MS assay indicated the reaction was complete. Water (0.27mL), NaOH (15% aq., 0.27 mL) and water (0.81 mL) were successively added to the above reaction mixture, which wasstirred at room temperature for 30 min, then dried over anhydrous Mg2SO4, and filtered. The filter cake was washed, and the filtrate was collected and concentrated under reduced pressure to afford compound TDI01155-2 (600 mg, crudeproduct).1H NMR (400 MHz, CDCl3) delta 8.43 (s, 1H), 7.49 (s, 1H), 7.42 (d, J = 8.4 Hz, 1H), 7.20 (m, 1H), 6.36 (s, 1H), 4.93 - 4.74(m, 2H), 3.86 -3.68 (m, 1H). MS m/z (ESI): 228.0 [M+H].General procedure: To ethyl 1H-indole-2-carboxylate (1.3 g, 6.89 mmol) in THF at 0 .was added lithium aluminumhydride solution (1M, in THF 0.29 g, 1.54 mmol) dropwise and the reaction mixture was stirred for 3.5 hours at0 . The reaction mixture was quenched with H2O, 15% NaOH, and H2O before it was filtered and rinsed withTHF. Reaction mixture was dried (anhydrous Na2SO4) and evaporation of the solvent gave 1.1 g (96% yield) of thecrude (1H-indol-2-yl)methanol which was used directly in the next step.General procedure: To a stirred solution of the crude (1H-indol-2-yl)methanol (1.07 g, 7.3 mmol) in anhydrous CH2Cl2(10 mL) at coldbath temperature (~10 .) was added portionwise pyridinium chlorochromate (PCC) (1.89 g, 8.1mmol). Reaction was stirred at ambient temperature for 2 hours. Reaction was diluted with CH2Cl2 and filteredthrough a pad of celite and washed with CH2Cl2. After evaporation of solvent, crude product was silica-columnchromatographed (Biotage) using Acetone: Hexane as an eluent to yield 1H-indole-2-carbaldehyde (2d) (0.43 g, 41% yield).

Molecular Weight:226.07
XLogP3:1.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:224.97893
Monoisotopic Mass:224.97893
Topological Polar Surface Area:36
Heavy Atom Count:12
Complexity:165
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes