3-Pyridinylboronic acid → HCID 24874607, compound

HRID 2264737Notes

Reaction equation

HRID 2264737 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.Br[C:11]1[CH:12]=[C:13]([C:17]2([C:28]3[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=3)[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([F:26])[CH:24]=3)[C:19]([NH2:27])=[N:18]2)[CH:14]=[CH:15][CH:16]=1>>[F:26][C:23]1[CH:24]=[C:25]2[C:20]([C:19]([NH2:27])=[N:18][C:17]2([C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)[C:13]2[CH:12]=[CH:11][CH:16]=[C:15]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH:14]=2)=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 59596286HCID 59596286, compound

Product 1

HCID 24874607HCID 24874607, compound

Procedure

The title compound was prepared as described in Example 78 (Scheme #14, N) using pyridin-3-ylboronic acid and 1-(3-bromophenyl)-6-fluoro-1-pyridin-4-yl-1H-isoindol-3-amine (Example 82) (18.5% yield): 1H NMR (DMSO-d6) δ 8.77 (m, 1 H), 8.55 (dd, J=4.80, 1.52 Hz, 1 H), 8.46 (m, 2 H), 7.95 (m, 1 H), 7.87-7.81 (m, 2 H), 7.59 (m, 2 H), 7.47 (m, 1 H), 7.39-7.44 (m, 2 H), 7.37-7.31 (m, 3 H), 6.96 (br s, 2 H); MS (ESI) m/z 381 [M+1]+.

Sources & evidence

ORD record
ord-44d802a9936e41fdb43ce578451a2b43
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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