4-t-Butylbenzenesulfonyl chloride → HCID 11259430, compound

HRID 2118140Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15]CC)=[O:14])=[C:7]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([O-])=O.[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:1][C:4]2[CH:5]=[C:6]3[C:10](=[CH:11][CH:12]=2)[NH:9][C:8]([C:13]([OH:15])=[O:14])=[C:7]3[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=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 741309ethyl 5-nitro-3-phenyl-1H-indole-2-carboxylate

Product 1

HCID 11259430HCID 11259430, compound

Procedure

The title compound was prepared from ethyl 5-nitro-3-phenyl-1H-indole-2-carboxylate and 4-tert-butylbenzene sulfonyl chloride followed the procedures of Example 1 Step 2 & Step 3 as a gray solid: 1H NMR (DMSO-d6) δ 1.25 (s, 9H, 7.05 (d, J=1.8 Hz, 1H, 7.10 (dd, J=8.9, 2.0 Hz, 1H, 7.26-7.45 (m, 6H, 7.54 (d, J=8.9 Hz, 2H, 7.57 (d, J=8.8 Hz, 2H, 9.81 (s, 1H, 11.79 (s, 1H, 12.42 (br s, 1H; MS (ESI) m/z 447 [M-H]−; HRMS calcd for C25H25N2O4S: 449.1533; found (ESI+): 449.1524; Anal. calcd for C25H24N2O4S.0.25H2O: C, 66.27; H, 5.45; N, 6.18. Found: C, 65.98; H, 5.34; N, 6.14.

Sources & evidence

ORD record: ord-068afb034f544af7bbc09985e6e32404
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442805B2

Reaction notes

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