3-Chlorobenzenesulphonyl chloride → HCID 68695396, compound

HRID 2235087Notes

Reaction equation

HRID 2235087 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[CH:22]=[C:21]3[C:17]([CH2:18][CH2:19][NH:20]3)=[CH:16][CH:15]=2)=[O:13])=[CH:7][C:6]=1[F:23])[CH3:2].[Cl:25][C:26]1[CH:27]=[C:28]([S:32](Cl)(=[O:34])=[O:33])[CH:29]=[CH:30][CH:31]=1>>[CH2:1]([O:3][C:4](=[O:24])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[CH:22]=[C:21]3[C:17]([CH2:18][CH2:19][N:20]3[S:32]([C:28]3[CH:29]=[CH:30][CH:31]=[C:26]([Cl:25])[CH:27]=3)(=[O:34])=[O:33])=[CH:16][CH:15]=2)=[O:13])=[CH:7][C:6]=1[F:23])[CH3:2]

Participants

3

Reactant 2

HCID 179093-Chlorobenzenesulphonyl chlorideHCID 68697366HCID 68697366, compound

Product 1

HCID 68695396HCID 68695396, compound

Procedure

4-{[1-(3-Chloro-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carbonyl]-amino}-2-fluoro-benzoic acid, m/z (ES+): 475.18 (M+H+.), was prepared in analogy to example 1, steps 1 to 5. Step 2 was performed using 4-amino-2-fluorobenzoic acid ethyl ester and yielded 2-fluoro-4-[(1H-indole-6-carbonyl)-amino]-benzoic acid ethyl ester. This was reduced to 4-[(2,3-dihydro-1H-indole-6-carbonyl)-amino]-2-fluoro-benzoic acid ethyl ester in step 3. Step 4 was performed using 3-chloro-benzenesulfonyl chloride, yielding 4-{[1-(3-chloro-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carbonyl]-amino}-2-fluoro-benzoic acid ethyl ester, which was hydrolyzed in step 5.

Sources & evidence

ORD record
ord-e8d5b40016214750bd6bff752f4789ba
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

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