4-Borono-3-methylbenzoic acid → 4-(5-Fluoro-6-hydroxyquinolin-2-yl)-3-methylbenzoic acid

HRID 1507399Notes

Reaction equation

HRID 1507399 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:13])[C:8]=2[F:12])[N:3]=1.B([C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][C:18]=1[CH3:26])(O)O>>[F:12][C:8]1[C:7]([OH:13])=[CH:6][CH:5]=[C:4]2[C:9]=1[CH:10]=[CH:11][C:2]([C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][C:18]=1[CH3:26])=[N:3]2

Participants

3

Reactant 2

HCID 221158924-Borono-3-methylbenzoic acidHCID 866980752-Chloro-5-fluoroquinolin-6-ol2×

Product 1

HCID 574048794-(5-Fluoro-6-hydroxyquinolin-2-yl)-3-methylbenzoic acid

Procedure

Followed the procedure described for Example 70, starting from 2-chloro-5-fluoroquinolin-6-ol (Intermediate 16) and 4-borono-3-methylbenzoic acid. 1H-NMR (DMSO-d6, 300 MHz, TMS): δ 13.03 (b, 1H), 10.47 (b, 1H), 8.43 (d, 1H), 7.93 (s, 1H), 7.90 (d, 1H), 7.78 (d, 1H), 7.72 (d, 1H), 7.62 (d, 1H), 7.52 (t, 1H), 2.43 (s, 3H). MS (ESI): m/z=296.38 [M−1]−.

Sources & evidence

ORD record
ord-8153c37a030f4ca8b7439cce1261ef6c
Source dataset
uspto-grants-2015_12
Patent number
US09221810B2

Reaction notes

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