2-Fluoropyridine-3-boronic acid → HCID 24874820, compound

HRID 2264763Notes

Reaction equation

HRID 2264763 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([Cl:24])[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:25][C:26]1[C:31](B(O)O)=[CH:30][CH:29]=[CH:28][N:27]=1>>[Cl:24][C:20]1[CH:19]=[C:18]([C:8]2([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([C:31]4[C:26]([F:25])=[N:27][CH:28]=[CH:29][CH:30]=4)[CH:3]=3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([NH2:17])=[N:9]2)[CH:23]=[CH:22][N:21]=1

Participants

3

Reactant 2

HCID 27832702-Fluoropyridine-3-boronic acidHCID 59596297HCID 59596297, compound

Product 1

HCID 24874820HCID 24874820, compoundYield 35%

Procedure

The title compound was synthesized from 1-(3-bromophenyl)-1-(2-chloropyridin-4-yl)-1H-isoindol-3-amine (Example 120) as described in Example 67 Scheme #10, D in 35% yield using 2-fluoropyridine-3-boronic acid. 1H NMR (DMSO-d6) δ 8.32 (d, J=5.31 Hz, 1 H), 8.27-8.19 (m, 1 H), 8.08-7.99 (m, 1 H), 7.96-7.81 (m, 2 H), 7.61-7.31 (m, 9 H), 7.01 (br s, 2 H); MS (ESI) m/z 415 [M+1]+.

Sources & evidence

ORD record
ord-dc7442c3c384446ca60890fb80805efe
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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