HCID 10199517, compound → HCID 10270246, compound

HRID 2184016Notes

Reaction equation

HRID 2184016 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](C2N3C=CC(C(F)(F)F)=NC3=NC=2)=[CH:4][C:3]=1[C:21]1[C:26]([F:27])=[CH:25][CH:24]=[CH:23][N:22]=1.Br[C:29]1[N:33]2[CH:34]=[CH:35][C:36]([C:38]([OH:41])([CH3:40])[CH3:39])=[N:37][C:32]2=[N:31][CH:30]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:29]2[N:33]3[CH:34]=[CH:35][C:36]([C:38]([OH:41])([CH3:40])[CH3:39])=[N:37][C:32]3=[N:31][CH:30]=2)=[CH:4][C:3]=1[C:21]1[C:26]([F:27])=[CH:25][CH:24]=[CH:23][N:22]=1

Participants

3

Reactant 2

HCID 10199517HCID 10199517, compoundHCID 112422822-(3-Bromoimidazo[1,2-a]pyrimidin-7-yl)propan-2-ol

Product 1

HCID 10270246HCID 10270246, compound

Procedure

4-Fluoro-3-(3-fluoropyridin-2-yl)phenylboronic acid (prepared according to Example 80) 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 3.5% methanol, gave 2-[3-(4-fluoro-3-(3-fluoropyridin-2-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol which was converted to its hydrochloride salt by treatment with methanolic hydrogen chloride, evaporation, and crystallisation of the residue from isopropanol/ethyl acetate: δH (400 MHz, DMSO) 1.56 (6H, s), 7.62-7.71 (1H, m), 7.70 (1H, dd, J 9 and 2), 7.87 (1H, d, J 7.4), 7.92-8.00 (3H, m), 8.54 (1H, s), 8.61 (1H, m), 9.25 (1H, d, J 7); m/z (ES+) 367 (MH+).

Workup

  1. customPurification by chromatography on silica gel
  2. washeluting with dichloromethane containing 3.5% methanol

Sources & evidence

ORD record
ord-b383c2a5542c435f9f923e8b6da59e34
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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