2-(3-Bromoimidazo[1,2-a]pyrimidin-7-yl)propan-2-ol → HCID 10293389, compound

HRID 2184022Notes

Reaction equation

HRID 2184022 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][C:3]=1[C:11]1[C:16]([F:17])=[CH:15][C:14]([F:18])=[CH:13][N:12]=1.Br[C:20]1[N:24]2[CH:25]=[CH:26][C:27]([C:29]([OH:32])([CH3:31])[CH3:30])=[N:28][C:23]2=[N:22][CH:21]=1>>[F:17][C:16]1[C:11]([C:3]2[CH:4]=[C:5]([C:20]3[N:24]4[CH:25]=[CH:26][C:27]([C:29]([OH:32])([CH3:30])[CH3:31])=[N:28][C:23]4=[N:22][CH:21]=3)[CH:6]=[CH:7][C:2]=2[F:1])=[N:12][CH:13]=[C:14]([F:18])[CH:15]=1

Participants

3

Reactant 2

HCID 112422822-(3-Bromoimidazo[1,2-a]pyrimidin-7-yl)propan-2-olHCID 116374193-(3,5-Difluoro-pyridin-2-yl)-4-fluorophenylboronic acid

Product 1

HCID 10293389HCID 10293389, compound

Procedure

4-Fluoro-3-(3,5-difluoropyridin-2-yl)phenylboronic acid was coupled with 2-(3-bromoimidazo[1,2-α]pyrimidin-7-yl)propan-2-ol by the method of Example 78. Purification by chromatography on silica gel eluting with dichloromethane containing 4% methanol and crystallisation from toluene/isohexane gave 2-[3-(3-(3,5-difluoropyridin-2-yl)-4-fluorophenyl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol: δH (400 MHz, DMSO) 8.96 (1H, d, J 7), 8.72 (1H, d, J 2), 8.17 (1H, dd, J 2 and 1), 7.93 (1H, s), 7.85-7.91 (2H, m), 7.59 (1H, dd, J 10 and 8), 7.40 (1H, d, J 7), 5.51 (1H, s), 1.51 (6H, s); m/z (ES+) 385 (MH+).

Workup

  1. customPurification by chromatography on silica gel eluting
  2. customwith dichloromethane containing 4% methanol and crystallisation from toluene/isohexane

Sources & evidence

ORD record
ord-dbc9c61e54d744ccbe09af1274e14d2d
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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