Benzenesulfonyl chloride → HCID 11261480, compound

HRID 2118129Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:14][CH:13]=1)[C:6]([C:24]([O:26]CC)=[O:25])=[C:5]2[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[C:35]1([S:41](Cl)(=[O:43])=[O:42])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>>[C:15]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:17][C:12]([CH2:11][N:7]2[C:8]3[C:4](=[CH:3][C:2]([NH:1][S:41]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)(=[O:43])=[O:42])=[CH:10][CH:9]=3)[C:5]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[C:6]2[C:24]([OH:26])=[O:25])=[CH:13][CH:14]=1

Participants

Reactant 2

HCID 7369Benzenesulfonyl chloride

HCID 69231659HCID 69231659, compound

Product 1

HCID 11261480HCID 11261480, compound

Procedure

The title compound was prepared from ethyl 5-amino-1-(1,1′-biphenyl-4-ylmethyl)-3-phenyl-1H-indole-2-carboxylate and phenylsulfonyl chloride followed the procedure of Example 1 Step 3 as a pale yellow solid: 1H NMR (DMSO-d6) δ 5.81 (s, 2H; 7.05-7.10 (m, 1H), 7.16 (d, J=8.3 Hz, 2H, 7.27 (d, J=8.3 Hz, 2H, 7.30-7.40 (m, 2H, 7.40-7.50 (m, 4H, 7.50-7.70 (m, 11H, 9.93 (s, 1H, 13.03 (br s, 1H; MS (ESI) m/z 557 [M-H]−; HRMS calcd for C34H27N2O4S: 559.1689; found (ESI+): 559.1688; Anal. calcd for C34H26N2O4S.0.5H2O: C, 71.94; H, 4.79; N, 4.94. Found: C, 71.81; H, 4.79; N, 5.07.

Sources & evidence

ORD record: ord-d7550497c4b84c37bcbba04a9c337e3d
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442805B2

Reaction notes

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