2-Fluoropyridine-3-boronic acid → HCID 24874825, compound

HRID 2264769Notes

Reaction equation

HRID 2264769 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]2([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([CH3:27])[CH:20]=3)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([NH2:18])=[N:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[F:28][C:29]1[C:34](B(O)O)=[CH:33][CH:32]=[CH:31][N:30]=1>>[F:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([CH3:27])[CH:20]=3)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([NH2:18])=[N:10]2)=[CH:3][C:2]=1[C:34]1[C:29]([F:28])=[N:30][CH:31]=[CH:32][CH:33]=1

Participants

3

Reactant 2

HCID 27832702-Fluoropyridine-3-boronic acidHCID 59596235HCID 59596235, compound

Product 1

HCID 24874825HCID 24874825, compoundYield 5%

Procedure

The title compound was synthesized from 1-(3-bromo-4-fluorophenyl)-1-(4-methoxy-3-methylphenyl)-1H-isoindol-3-amine (Example 126) as described in Example 67 Scheme #10, D in 5% yield using 2-fluoropyridine-3-boronic acid. 1H NMR (DMSO-d6) δ 8.54-8.46 (m, 1 H), 8.22-8.15 (m, 1 H), 8.05-7.84 (m, 2 H), 7.76-7.55 (m, 5 H), 7.53-7.41 (m, 1 H), 7.32-7.23 (m, 2 H), 7.08-6.78 (m, 3 H), 3.93 (s, 3 H), 2.27 (s, 3 H); MS (ESI) m/z 442 [M+1]+.

Sources & evidence

ORD record
ord-8f6b3c4af380490b9424f75ee4620bd3
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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