2-(3-Bromoimidazo[1,2-a]pyrimidin-7-yl)propan-2-ol → HCID 69708462, compound

HRID 2184052Notes

Reaction equation

HRID 2184052 reaction equation
CC1(C)COB([C:8]2[CH:9]=[CH:10][C:11]([F:23])=[C:12]([C:14]3[CH:22]=[N:21][CH:20]=[CH:19][C:15]=3[C:16]([NH2:18])=[O:17])[CH:13]=2)OC1.Br[C:26]1[N:30]2[CH:31]=[CH:32][C:33]([C:35]([OH:38])([CH3:37])[CH3:36])=[N:34][C:29]2=[N:28][CH:27]=1>>[F:23][C:11]1[CH:10]=[CH:9][C:8]([C:26]2[N:30]3[CH:31]=[CH:32][C:33]([C:35]([OH:38])([CH3:36])[CH3:37])=[N:34][C:29]3=[N:28][CH:27]=2)=[CH:13][C:12]=1[C:14]1[CH:22]=[N:21][CH:20]=[CH:19][C:15]=1[C:16]([NH2:18])=[O:17]

Participants

3

Reactant 2

HCID 112422822-(3-Bromoimidazo[1,2-a]pyrimidin-7-yl)propan-2-olHCID 22473570HCID 22473570, compound

Product 1

HCID 69708462HCID 69708462, compound

Procedure

3-[5-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-2-fluorophenyl]isonicotinamide (100 mg, 0.41 mmol) was coupled to 2-(3-bromoimidazo[1,2-α]pyrimidin-7-yl)propan-2-ol (106 mg, 0.41 mmol) using the method in Example 1. Purification by chromatography on silica gel eluting with dichloromethane containing 8% methanol then trituration with diethyl ether gave 3-{2-fluoro-5-[7-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyrimidin-3-yl]phenyl}isonicotinamide as a white solid: δH (400 MHz, CDCl3) 1.58 (6H, s), 4.42 (1H, s), 5.68 (1H, s), 5.82 (1H, s), 7.08 (1H, d, J 7), 7.36 (1H, t, J 7), 7.57-7.61 (3H, m), 7.86 (1H, s), 8.71 (1H, d, J 7), 8.74 (1H, s), 8.78 (1H, d, J 5); m/z (ES+) 392 (M++H).

Workup

  1. customPurification by chromatography on silica gel eluting with dichloromethane containing 8% methanol

Sources & evidence

ORD record
ord-6caa222867f8439ca3919d8513dc83e4
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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