Thiophene-3-boronic acid → HCID 10222374, compound

HRID 2183899Notes

Reaction equation

HRID 2183899 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:12]=[CH:13][C:14]([F:25])=[C:15]([C:17]4[C:18]([C:23]#[N:24])=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:16]=3)=[CH:9][N:10]=[C:4]2[N:3]=1.[S:26]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27]1>>[F:25][C:14]1[CH:13]=[CH:12][C:11]([C:8]2[N:5]3[CH:6]=[CH:7][C:2]([C:28]4[CH:29]=[CH:30][S:26][CH:27]=4)=[N:3][C:4]3=[N:10][CH:9]=2)=[CH:16][C:15]=1[C:17]1[C:18]([C:23]#[N:24])=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 581760Thiophene-3-boronic acidHCID 10291444HCID 10291444, compound

Product 1

HCID 10222374HCID 10222374, compoundYield 77.6%

Procedure

5′-(7-Chloroimidazo[1,2-α]pyrimidin-3-yl)-2′-fluorobiphenyl-2-carbonitrile (50 mg, 0.143 mmol) and 3-thiopheneboronic acid (346 mg, 0.287 mmol) were reacted using the procedure in Example 23 to give 2′-fluoro-5′-[7-(thien-3-yl)imidazo[1,2-α]pyrimidin-3-yl]biphenyl-2-carbonitrile (44 mg, 77%) as a yellow powder: δH (400 MHz, CDCl3) 7.31 (1H, d, J 7), 7.39-7.45 (2H, m), 7.55 (1H, dt, J 9 and 1), 7.61-7.67 (3, m), 7.71 (1H, dt, J 8 and 1), 7.84-7.90 (3H, m), 8.11 (1H, s), 8.82 (1H, d, J 7); m/z (ES+) 397 (M++H).

Sources & evidence

ORD record
ord-e7288ccae9554c10af20ff89ee20b583
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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