5-Chloro-2-methoxybenzene-1-sulfonyl chloride → HCID 68696968, compound

HRID 2235106Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:35][CH3:36])=[C:6]([S:8]([N:11]2[C:19]3[C:14](=[C:15]([O:33][CH3:34])[CH:16]=[C:17]([C:20]([NH:22][C:23]4[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[C:25]([F:32])[CH:24]=4)=[O:21])[CH:18]=3)[CH2:13][CH2:12]2)(=[O:10])=[O:9])[CH:7]=1.Cl[C:38]1C=CC(OC)=C(S(Cl)(=O)=O)[CH:43]=1>>[CH2:38]([O:28][C:27](=[O:29])[C:26]1[CH:30]=[CH:31][C:23]([NH:22][C:20]([C:17]2[CH:18]=[C:19]3[C:14]([CH2:13][CH2:12][N:11]3[S:8]([C:6]3[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[O:35][CH3:36])(=[O:10])=[O:9])=[C:15]([O:33][CH3:34])[CH:16]=2)=[O:21])=[CH:24][C:25]=1[F:32])[CH3:43]

Participants

Reactant 2

HCID 27342725-Chloro-2-methoxybenzene-1-sulfonyl chloride

HCID 16051659HCID 16051659, compound

Product 1

HCID 68696968HCID 68696968, compound

Procedure

4-{[1-(5-Chloro-2-methoxy-benzenesulfonyl)-4-methoxy-2,3-dihydro-1H-indole-6-carbonyl]-amino}-2-fluoro-benzoic acid, m/z (ES+): 535.33 (M+H+.), was prepared in analogy to example 14, steps 1 to 6. Step 5 was performed using 5-chloro-2-methoxy-benzenesulfonyl chloride and yielded 4-{[1-(5-chloro-2-methoxy-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-95bad3e0c56449e5b7841111495c3302
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713996B2

Reaction notes

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