3-Bromo-7-methylimidazo[1,2-a]pyrimidine → HCID 9880485, compound

HRID 2183867Notes

Reaction equation

HRID 2183867 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH3:11])=[N:10][C:5]2=[N:4][CH:3]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16](B2OC(C)(C)C(C)(C)O2)=[CH:15][C:14]=1[C:28]1[C:29]([C:34]#[N:35])=[CH:30][CH:31]=[CH:32][CH:33]=1>>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:2]2[N:6]3[CH:7]=[CH:8][C:9]([CH3:11])=[N:10][C:5]3=[N:4][CH:3]=2)=[CH:15][C:14]=1[C:28]1[C:29]([C:34]#[N:35])=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

3

Reactant 2

HCID 114015833-Bromo-7-methylimidazo[1,2-a]pyrimidineHCID 117716472′-Fluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-2-carbonitrile

Product 1

HCID 9880485HCID 9880485, compound

Procedure

3-Bromo-7-methylimidazo[1,2-α]pyrimidine was coupled with 2′-fluoro-5′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile as described in Example 1 to give 2′-fluoro-5′-(7-methylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile. Purification by high performance liquid chromatography afforded the trifluoroacetate salt as a white powder: δH (400 MHz, DMSO) 2.60 (3H, s), 7.11 (1H, d, J 7), 7.59-7.70 (2H, m), 7.76 (1H, d, J 8), 7.84-7.89 (3H, m), 8.00-8.04 (2H, m), 9.00 (1H, d, J 7); m/z (ES+) 329 (M++H).

Sources & evidence

ORD record
ord-184a19ecf87b4eb9a8955590b49090ce
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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