2-Fluoropyridine-3-boronic acid → 1-[3-(2-Fluoropyridin-3-yl)phenyl]-1-(2-methoxypyrimidin-5-yl)-1H-isoindol-3-amine

HRID 2264754Notes

Reaction equation

HRID 2264754 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:18]3[CH:19]=[N:20][C:21]([O:24][CH3:25])=[N:22][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: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]=[N:22][C:21]([O:24][CH3:25])=[N:20][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 59596264HCID 59596264, compound

Product 1

HCID 248747391-[3-(2-Fluoropyridin-3-yl)phenyl]-1-(2-methoxypyrimidin-5-yl)-1H-isoindol-3-amineYield 34%

Procedure

The title compound was synthesized from 1-(3-bromophenyl)-1-(2-methoxypyrimidin-5-yl)-1H-isoindol-3-amine (Example 106) as described in Example 67 Scheme #10, D in 34% yield using 2-fluoropyridine-3-boronic acid. 1H NMR (DMSO-d6) δ 8.47 (s, 2 H), 8.19-8.13 (m, 1 H), 8.01-7.91 (m, 1 H), 7.88-7.81 (m, 1 H), 7.77 (d, J=5.56 Hz, 1 H), 7.52-7.48 (m, 1 H), 7.46-7.32 (m, 6 H), 6.88 (br s, 2 H), 3.80 (s, 3 H); MS (ESI) m/z 412 [M+1]+.

Sources & evidence

ORD record
ord-3d9006d728004c37a12ec49ab3c21160
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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