Ethyl 4-Amino-2-fluorobenzoate → HCID 68699374, compound

HRID 2235086Notes

Reaction equation

ClC1C=C(S([N:11]2[C:19]3[C:14](=[CH:15][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)=O)C=CC=1.[CH2:33](OC(=O)C1C=CC(N)=CC=1F)[CH3:34]>>[CH2:33]([O:29][C:27](=[O:28])[C:26]1[CH:30]=[CH:31][C:23]([NH:22][C:20]([C:17]2[CH:18]=[C:19]3[C:14]([CH:13]=[CH:12][NH:11]3)=[CH:15][CH:16]=2)=[O:21])=[CH:24][C:25]=1[F:32])[CH3:34]

Participants

Reactant 2

HCID 10797532Ethyl 4-Amino-2-fluorobenzoate

HCID 16051557HCID 16051557, compound

Product 1

HCID 68699374HCID 68699374, 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-0f43ca7b9bc14fc8bceadbb08df838dd
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713996B2

Reaction notes

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