Acetyl chloride → (1-Benzyl-5-bromo-1H-indol-2-yl)methyl acetate

HRID 2373500Notes

Reaction equation

HRID 2373500 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([Br:17])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH2:18][OH:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20](Cl)(=[O:22])[CH3:21]>>[C:20]([O:19][CH2:18][C:9]1[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:16]2[C:11]([CH:10]=1)=[CH:12][C:13]([Br:17])=[CH:14][CH:15]=2)(=[O:22])[CH3:21]

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 21964298(1-Benzyl-5-bromo-1H-indol-2-yl)methanol

Product 1

HCID 21964295(1-Benzyl-5-bromo-1H-indol-2-yl)methyl acetate

Procedure

The title compound was prepared from (1-benzyl-5-bromo-1H-indol-2-yl)methanol and acetyl chloride in substantially the same manner, as described in step 4 of Example 1. The product was obtained as a semi-solid. Mass spectrum (ESI, [M−H]−) m/z 356. 1H NMR (400 MHz, DMSO-d6) δ 7.78 (d, 1H, J=2.13 Hz), 7.38 (d, 1H, J=8.86 Hz), 7.29-7.20 (m, 4H), 6.94 (d, 2H, J=7.17 Hz), 6.64 (s, 1H), 5.47 (s, 2H), 5.21 (s, 2H), and 1.79 ppm (s, 3H).

Workup

  1. customThe product was obtained as a semi-solid

Sources & evidence

ORD record
ord-736bf5609e4b43ffad8c1d73b4deb1e0
Source dataset
uspto-grants-2008_12
Patent number
US07459478B2

Reaction notes

Loading…