2-Fluoropyridine-3-boronic acid → HCID 24874783, compound

HRID 2264762Notes

Reaction equation

HRID 2264762 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([O:24][CH3:25])[CH:19]=3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([NH2:17])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[F:26][C:27]1[C:32](B(O)O)=[CH:31][CH:30]=[CH:29][N:28]=1>>[F:26][C:27]1[C:32]([C:2]2[CH:3]=[C:4]([C:8]3([C:18]4[CH:23]=[CH:22][N:21]=[C:20]([O:24][CH3:25])[CH:19]=4)[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[C:10]([NH2:17])=[N:9]3)[CH:5]=[CH:6][CH:7]=2)=[CH:31][CH:30]=[CH:29][N:28]=1

Participants

3

Reactant 2

HCID 27832702-Fluoropyridine-3-boronic acidHCID 59596262HCID 59596262, compound

Product 1

HCID 24874783HCID 24874783, compoundYield 23%

Procedure

The title compound was synthesized from 1-(3-bromophenyl)-1-(2-methoxypyridin-4-yl)-1H-isoindol-3-amine (Example 118) as described in Example 67 Scheme #10, D in 23% yield using 2-fluoropyridine-3-boronic acid. 1H NMR (DMSO-d6) δ 8.20-8.26 (m, 1 H), 7.97-8.09 (m, 2 H), 7.75-7.92 (m, 2 H), 7.37-7.58 (m, 7 H), 6.78-7.10 (m, 3 H), 6.67 (s, 1 H), 3.79 (s, 3 H); MS (ESI) m/z 411 [M+1]+.

Sources & evidence

ORD record
ord-91d0a33726b24633801941042617aaff
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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