2-(3-Bromoimidazo[1,2-a]pyrimidin-7-yl)propan-2-ol → HCID 69707828, compound

HRID 2184064Notes

Reaction equation

HRID 2184064 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][C:3]=1[N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.Br[C:17]1[N:21]2[CH:22]=[CH:23][C:24]([C:26]([OH:29])([CH3:28])[CH3:27])=[N:25][C:20]2=[N:19][CH:18]=1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:17]2[N:21]3[CH:22]=[CH:23][C:24]([C:26]([OH:29])([CH3:27])[CH3:28])=[N:25][C:20]3=[N:19][CH:18]=2)=[CH:4][C:3]=1[N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Participants

3

Reactant 2

HCID 112422822-(3-Bromoimidazo[1,2-a]pyrimidin-7-yl)propan-2-olHCID 223294894-Fluoro-3-([1,2,4]triazol-1-yl)phenylboronic acid

Product 1

HCID 69707828HCID 69707828, compound

Procedure

4-Fluoro-3-([1,2,4]triazol-1-yl)phenylboronic acid (100 mg, 0.48 mmol) was coupled to 2-(3-bromoimidazo[1,2-α]pyrimidin-7-yl)propan-2-ol (113 mg, 0.44 mmol) using the method in Example 1. Purification by chromatography on silica gel eluting with dichloromethane containing 5% methanol then trituration with diethyl ether gave 2-[3-(4-fluoro-3-([1,2,4]triazol-1-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol as a pink solid: δH (400 MHz, CDCl3) 1.63 (6H, s), 4.31 (1H, s), 7.12 (1H, d, J 7), 7.47-7.57 (2H, m), 7.91 (1H, s), 8.14-8.18 (2H, m), 8.61 (1H, d, J 7), 8.79 (1H, d, J 3); m/z (ES+) 339 (M++H).

Workup

  1. customPurification by chromatography on silica gel eluting with dichloromethane containing 5% methanol

Sources & evidence

ORD record
ord-83c26fae07804c24b1090d19b141dfc5
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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