2-(3-Bromoimidazo[1,2-a]pyrimidin-7-yl)propan-2-ol → HCID 67486613, compound

HRID 2184066Notes

Reaction equation

HRID 2184066 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]([OH:14])([CH3:13])[CH3:12])=[N:10][C:5]2=[N:4][CH:3]=1.[F:15][C:16]1[CH:17]=[N:18][CH:19]=[C:20]([C:22]2[CH:27]=[C:26](B3OC(C)(C)C(C)(C)O3)[CH:25]=[CH:24][C:23]=2[F:37])[CH:21]=1>>[F:37][C:23]1[CH:24]=[CH:25][C:26]([C:2]2[N:6]3[CH:7]=[CH:8][C:9]([C:11]([OH:14])([CH3:13])[CH3:12])=[N:10][C:5]3=[N:4][CH:3]=2)=[CH:27][C:22]=1[C:20]1[CH:19]=[N:18][CH:17]=[C:16]([F:15])[CH:21]=1

Participants

3

Reactant 2

HCID 112422822-(3-Bromoimidazo[1,2-a]pyrimidin-7-yl)propan-2-olHCID 22473595HCID 22473595, compound

Product 1

HCID 67486613HCID 67486613, compoundYield 21%

Procedure

2-(3-Bromoimidazo[1,2-α]pyrimidin-7-yl)propan-2-ol was coupled with 3-fluoro-5-[2-fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]pyridine as described in Example 65 to give 2-{3-[4-fluoro-3-(5-fluoropyridin-3-yl)phenyl]imidazo[1,2-α]pyrimidin-7-yl}propan-2-ol as an off-white solid (30 mg, 21%). Bis-hydrochloride salt (from ethyl acetate: ethanol (1:1)): δH (360 MHz, d6-DMSO) 1.56 (6H, s), 7.67-7.73 (1H, m), 7.83-7.89 (2H, m), 8.05-8.07 (1H, m), 8.11-8.15 (1H, m), 8.51 (1H, s), 8.71 (1H, s), 8.80 (1H, s), 9.36 (1H, d, J 7).

Sources & evidence

ORD record
ord-ed8f1cc65a8a432299e6d51214f80832
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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