Acetyl chloride → HCID 21964296, compound

HRID 2373496Notes

Reaction equation

[C:1]([C:5]1[CH:24]=[CH:23][C:8]([CH2:9][N:10]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[CH:12]=[C:11]2[CH2:21][OH:22])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:25](Cl)(=[O:27])[CH3:26]>>[C:25]([O:22][CH2:21][C:11]1[N:10]([CH2:9][C:8]2[CH:23]=[CH:24][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6][CH:7]=2)[C:18]2[C:13]([CH:12]=1)=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)(=[O:27])[CH3:26]

Participants

Reactant 2

HCID 6367Acetyl chloride

HCID 21964299HCID 21964299, compound

Product 1

HCID 21964296HCID 21964296, compound

Procedure

The title compound was prepared from [1-(4-tert-butylbenzyl)-5-methoxy-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 white solid. Mass spectrum (ESI, [M+H]+) m/z 366. 1H NMR (400 MHz, DMSO-d6) δ 7.30 (s, 1H), 7.28 (d, 2H, J=8.10 Hz), 7.07 (d, 1H, J=2.45 Hz), 7.86 (d, 2H, J=8.24 Hz), 7.76 (dd, 1H, J=8.86 and 2.29 Hz), 6.54 (s, 1H), 5.36 (s, 2H), 5.18 (s, 2H), 3.74 (s, 3H), 1.77 (s, 3H), and 1.20 ppm (s, 9H).

Workup

customThe product was obtained as a white solid

Sources & evidence

ORD record: ord-87667136b3a846e8b4ac9140f6a8f67d
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459478B2

Reaction notes

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