2-Fluoropyridine-3-boronic acid → HCID 24874822, compound

HRID 2264765Notes

Reaction equation

HRID 2264765 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:18]3[CH:19]=[N:20][CH:21]=[C:22]([F:24])[CH:23]=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>>[F:24][C:22]1[CH:23]=[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:19]=[N:20][CH:21]=1

Participants

3

Reactant 2

HCID 27832702-Fluoropyridine-3-boronic acidHCID 59596288HCID 59596288, compound

Product 1

HCID 24874822HCID 24874822, compoundYield 26%

Procedure

The title compound was synthesized from 1-(3-bromophenyl)-1-(5-fluoropyridin-3-yl)-1H-isoindol-3-amine (Example 123) as described in Example 67 Scheme #10, D in 26% yield using 2-fluoropyridine-3-boronic acid. 1H NMR (DMSO-d6) δ 8.35-8.45 (m, 2 H), 8.12-8.21 (m, 1 H), 7.92-8.01 (m, 1 H), 7.83-7.90 (m, 1 H), 7.73-7.82 (m, 1 H), 7.33-7.56 (m, 8 H), 6.91 (br s, 2 H); MS (ESI) m/z 399 [M+1]+.

Sources & evidence

ORD record
ord-67a54ffb15da48b6a7617cd9e4887a84
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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