p-(Trifluoromethoxy)benzenesulphonyl chloride → HCID 11213685, compound

HRID 2118139Notes

Reaction equation

HRID 2118139 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.[F:24][C:25]([F:38])([F:37])[O:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>>[C:18]1([C:7]2[C:6]3[C:10](=[CH:11][CH:12]=[C:4]([NH:1][S:33]([C:30]4[CH:29]=[CH:28][C:27]([O:26][C:25]([F:24])([F:37])[F:38])=[CH:32][CH:31]=4)(=[O:35])=[O:34])[CH:5]=3)[NH:9][C:8]=2[C:13]([OH:15])=[O:14])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 523102p-(Trifluoromethoxy)benzenesulphonyl chlorideHCID 741309ethyl 5-nitro-3-phenyl-1H-indole-2-carboxylate

Product 1

HCID 11213685HCID 11213685, compound

Procedure

The title compound was prepared from ethyl 5-nitro-3-phenyl-1H-indole-2-carboxylate and 4-trifluoromethoxy-benzenesulfonyl chloride followed the procedures of Example 1 Step 2 & Step 3 as a dark brown solid: 1H NMR (DMSO-d6) δ 7.01 (d, J=1.8 Hz, 1H), 7.06 (dd, J=8.7, 1.9 Hz, 1H, 7.28-7.42 (m, 6H, 7.50 (d, J=6.9 Hz, 2H, 7.74 (d, J=8.9 Hz, 2H, 9.94 (s, 1H, 11.84 (s, 1H, 12.89 (br s, 1H; MS (ESI) m/z 475 [M-H]−; HRMS calcd for C22H16F3N2O5S: 477.0730; found (ESI+): 477.0719; Anal. calcd for C22H15F3N2O5S.0.15H2O: C, 55.15; H, 3.22; N, 5.85. Found: C, 54.95; H, 3.23; N, 5.93.

Sources & evidence

ORD record
ord-01627a71bf1147e6ba67a87aa4a713d8
Source dataset
uspto-grants-2008_10
Patent number
US07442805B2

Reaction notes

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