4-t-Butylbenzenesulfonyl chloride → HCID 11328712, compound

HRID 916182Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=1)[CH:9]=[CH:8]2)=[O:4].[C:24]([C:28]1[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1)([CH3:27])([CH3:26])[CH3:25]>>[C:24]([C:28]1[CH:33]=[CH:32][C:31]([S:34]([NH:21][C:18]2[CH:19]=[CH:20][C:15]([CH2:14][N:10]3[C:11]4[C:7](=[CH:6][C:5]([C:3]([OH:2])=[O:4])=[CH:13][CH:12]=4)[CH:8]=[CH:9]3)=[CH:16][CH:17]=2)(=[O:36])=[O:35])=[CH:30][CH:29]=1)([CH3:27])([CH3:25])[CH3:26]

Participants

Reactant 2

HCID 1398824-t-Butylbenzenesulfonyl chloride

HCID 69436120HCID 69436120, compound

Product 1

HCID 11328712HCID 11328712, compound

Procedure

The title compound was prepared from 1-(4-nitro-benzyl)-1H-indole-5-carboxylic acid methyl ester and 4-tert-butylbenzene sulfonyl chloride followed the procedure of Example 3 Step 2 as a light brown solid: 1H NMR (DMSO-d6) δ 1.24 (s, 9H), 5.33 (s, 2H), 6.59 (d, J=3.2 Hz, 1H), 7.02 (d, J=8.7 Hz, 2H), 7.07 (d, J=8.7 Hz, 2H), 7.45 (d, J=8.7 Hz, 1H), 7.51-7.54 (m, 3H), 7.65 (d, J=8.5 Hz, 2H), 7.69 (d, J=1.7 Hz, 1H), 8.21 (d, J=1.3 Hz, 1H), 10.23 (br s, 1H), 12.39 (br s, 1H); MS (ESI) m/z 463 (MH+), 461 ([M−H]−); HRMS calcd for C26H26N2O4S: 463.1690; found (ESI+): 463.1681.

Sources & evidence

ORD record: ord-aa366428751f499b8d84ea086187a457
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268159B2

Reaction notes

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