Benzenesulfonyl chloride, 3,4-dichloro- → HCID 68695487, compound

HRID 2235105Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[C:20]3[C:15](=[C:16]([O:34][CH3:35])[CH:17]=[C:18]([C:21]([NH:23][C:24]4[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[C:26]([F:33])[CH:25]=4)=[O:22])[CH:19]=3)[CH2:14][CH2:13]2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl[C:37]1C=C(S(Cl)(=O)=O)C=C[C:42]=1Cl>>[CH2:37]([O:29][C:28](=[O:30])[C:27]1[CH:31]=[CH:32][C:24]([NH:23][C:21]([C:18]2[CH:19]=[C:20]3[C:15]([CH2:14][CH2:13][N:12]3[S:9]([C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)(=[O:10])=[O:11])=[C:16]([O:34][CH3:35])[CH:17]=2)=[O:22])=[CH:25][C:26]=1[F:33])[CH3:42]

Participants

Reactant 2

HCID 7383Benzenesulfonyl chloride, 3,4-dichloro-

HCID 16051658HCID 16051658, compound

Product 1

HCID 68695487HCID 68695487, compound

Procedure

4-{[1-(3,4-Dichloro-benzenesulfonyl)-4-methoxy-2,3-dihydro-1H-indole-6-carbonyl]-amino}-2-fluoro-benzoic acid, m/z (ES+): 539.27 (M+H+.), was prepared in analogy to example 14, steps 1 to 6. Step 5 was performed using 3,4-dichloro-benzenesulfonyl chloride and yielded 4-{[1-(3,4-dichloro-benzenesulfonyl)-4-methoxy-2,3-dihydro-1H-indole-6-carbonyl]-amino}-2-fluoro-benzoic acid ethyl ester, which was hydrolyzed in step 6.

Sources & evidence

ORD record: ord-cf652643aa234e6b86aff719e0ed3a3a
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713996B2

Reaction notes

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