(Pyrimidin-5-yl)boronic acid → HCID 24874823, compound

HRID 2264766Notes

Reaction equation

HRID 2264766 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.[N:25]1[CH:30]=[C:29](B(O)O)[CH:28]=[N:27][CH:26]=1>>[F:24][C:22]1[CH:23]=[C:18]([C:8]2([C:16]3[CH:11]=[CH:12][CH:13]=[C:14]([C:29]4[CH:30]=[N:25][CH:26]=[N:27][CH:28]=4)[CH:15]=3)[C:4]3[C:3](=[CH:2][CH:7]=[CH:6][CH:5]=3)[C:10]([NH2:17])=[N:9]2)[CH:19]=[N:20][CH:21]=1

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 59596288HCID 59596288, compound

Product 1

HCID 24874823HCID 24874823, compoundYield 41%

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 41% yield using pyrimidine-5-boronic acid. 1H NMR (DMSO-d6) δ 9.18 (s, 1 H), 9.04 (s, 2 H), 8.49 (t, J=1.77 Hz, 1 H), 8.45 (d, J=2.53 Hz, 1 H), 8.08-8.02 (m, 1 H), 7.90-7.80 (m, 1 H), 7.74-7.64 (m, 2 H), 7.62-7.43 (m, 5 H), 6.98 (br s, 2 H); MS (ESI) m/z 382 [M+1]+.

Sources & evidence

ORD record
ord-7fd7d046bd644347b9fcb37f509c4a44
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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