Aluminium lithium hydride → (1-Benzyl-5-bromo-1H-indol-2-yl)methanol

HRID 2373499Notes

Reaction equation

HRID 2373499 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([C:18](OCC)=[O:19])=[CH:5]2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[CH2:11]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([Br:1])=[CH:10][CH:9]=2)[CH:5]=[C:6]1[CH2:18][OH:19])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21964289Ethyl 1-benzyl-5-bromo-1H-indole-2-carboxylate

Product 1

HCID 21964298(1-Benzyl-5-bromo-1H-indol-2-yl)methanol

Procedure

The title compound was prepared from ethyl 5-bromo-1-benzyl-1H-indole-2-carboxylate and lithium aluminum hydride in substantially the same manner, as described in step 3 of Example 1. The product was obtained as a semi-solid. Mass spectrum (ESI, [M−H]−) m/z 314. 1H NMR (400 MHz, DMSO-d6) δ 7.67 (s, 1H), 7.58-7.15 (m, 4H), 7.12 (d, 1H, J=8.69 and 1.97 Hz), 6.98 (d, 2H, J=8.34 Hz) 6.41 (s, 1H), 5.43 (s, 2H), 5.33 (t, 1H, J=5.57 Hz), and 4.54 ppm (d, 2H, J=5.43 Hz).

Workup

  1. customThe product was obtained as a semi-solid

Sources & evidence

ORD record
ord-22464f1c83904fe7b341c14aaefa09f0
Source dataset
uspto-grants-2008_12
Patent number
US07459478B2

Reaction notes

Loading…