4-t-Butylbenzenesulfonyl chloride → HCID 11225025, compound

HRID 916186Notes

Reaction equation

C[O:2][C:3]([C:5]1[C:6]2[CH:7]=[CH:8][N:9]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=3)[C:10]=2[CH:11]=[CH:12][CH:13]=1)=[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:9]3[C:10]4[CH:11]=[CH:12][CH:13]=[C:5]([C:3]([OH:2])=[O:4])[C:6]=4[CH:7]=[CH:8]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 69435489HCID 69435489, compound

Product 1

HCID 11225025HCID 11225025, compound

Procedure

The title compound was prepared from 1-(4-nitro-benzyl)-1H-indole-4-carboxylic acid methyl ester and 4-tert-butylbenzenesulfonyl chloride followed the procedure of Example 3 Step 2 as a pale pink solid: 1H NMR (DMSO-d6) δ 1.24 (s, 9H), 5.35 (s, 2H), 6.96 (d, J=3.1 Hz, 1H), 7.03 (d, J=8.7 Hz, 2H), 7.07 (d, J=8.0 Hz, 2H), 7.15 (t, J=7.8 Hz, 1H), 7.53 (d, J=8.8 Hz, 2H), 7.57 (d, J=3.2 Hz, 1H), 7.62-7.68 (m, 3H), 7.70 (dd, J=7.5, 0.9 Hz, 1H), 10.26 (br s, 1H), 12.59 (br s, 1H); MS (ESI) m/z 463 (MH+), 461 ([M−H]−); HRMS calcd for C26H27N2O4S: 463.1690; found (ESI+): 463.1674.

Sources & evidence

ORD record: ord-707b9e7616df4dadacfb303da475835b
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268159B2

Reaction notes

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