Acetyl chloride → HCID 21964291, compound

HRID 2212154Notes

Reaction equation

[CH3:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=4)=[CH:13][CH:14]=3)[CH:9]=[C:8]2[CH2:23][OH:24])=[CH:4][CH:3]=1.[C:27](Cl)(=[O:29])[CH3:28]>>[C:27]([O:24][CH2:23][C:8]1[N:7]([CH2:6][C:5]2[CH:25]=[CH:26][C:2]([CH3:1])=[CH:3][CH:4]=2)[C:15]2[C:10]([CH:9]=1)=[CH:11][C:12]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=1)=[CH:13][CH:14]=2)(=[O:29])[CH3:28]

Participants

Reactant 2

HCID 6367Acetyl chloride

HCID 21964281HCID 21964281, compound

Product 1

HCID 21964291HCID 21964291, compound

Procedure

The title compound was prepared from [1-(4-methylbenzyl)-5-(3-methylphenyl)-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 brown oil. Mass spectrum (ESI, [M+H]+) m/z 384. 1H NMR (400 MHz, DMSO-d6) δ 7.82 (s, 1H), 7.47 (s, 1H), 7.45–7.40 (m, 3H), 7.31 (t, 1H, J=7.74 Hz), 7.13–7.08 (m, 3H), 6.90 (d, 2H, J=8.09 Hz), 6.68 (s, 1H), 5.43 (s, 2H), 5.22 (s, 2H), 2.36 (s, 3H), 2.23 (s, 3H), and 1.85 ppm (s, 3H).

Workup

customThe product was obtained as a brown oil

Sources & evidence

ORD record: ord-f7772b6636fe4a6aa914b982339110b0
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07101903B2

Reaction notes

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