Bromide ion → HCID 86297146, compound

HRID 930830Notes

Reaction equation

HRID 930830 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:12]=[C:13]([NH:18][C:19]([C:21]4[O:22][C:23]([CH3:26])=[CH:24][CH:25]=4)=[O:20])[CH:14]=[CH:15][C:16]=3[Cl:17])[N:10]=2)[CH:7]=1.[Br-].[C:28]1(B(O)O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CO>[Cl:17][C:16]1[CH:15]=[CH:14][C:13]([NH:18][C:19]([C:21]2[O:22][C:23]([CH3:26])=[CH:24][CH:25]=2)=[O:20])=[CH:12][C:11]=1[C:9]1[N:10]=[C:5]2[N:4]=[CH:3][C:2]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:7][N:6]2[CH:8]=1

Participants

5

Reactant 3

HCID 259Bromide ionHCID 66827Phenylboronic AcidHCID 90411755HCID 90411755, compound

Product 1

HCID 86297146HCID 86297146, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 31 was synthesized using N-(3-(6-bromoimidazo[1,2-a]pyrimidin-2-yl)-4-chlorophenyl)-5-methylfuran-2-carboxamide (I-14) as the bromide and phenylboronic acid using a suzuki coupling protocol described in the synthesis of I-11. The residue was redissolved in methanol and precipitation yielded the compound 1H NMR (400 MHz, DMSO-D6) δ 10.33 (s, 1H), 9.38 (d, J=2.1, 1H), 8.99 (d, J=2.0, 1H), 8.71 (d, J=2.5, 1H), 8.62 (s, 1H), 7.95 (dd, J=2.4, 8.7, 1H), 7.80 (d, J=7.8, 2H), 7.52 (dt, J=7.8, 14.7, 5H), 7.34 (d, J=3.3, 1H), 6.35 (d, J=3.3, 1H), 2.40 (s, 3H).

Workup

  1. customdescribed in the synthesis of I-11
  2. customprecipitation

Sources & evidence

ORD record
ord-b6b292d9f42d40068bed8f090948b583
Source dataset
uspto-grants-2016_03
Patent number
US09296754B2

Reaction notes

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