3'-Fluoro-5'-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile → 3'-Fluoro-5'-(7-hydroxymethylimidazo[1,2-alpha]pyrimidin-3-yl)biphenyl-2-carbonitrile

HRID 2183917Notes

Reaction equation

HRID 2183917 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH2:11][OH:12])=[N:10][C:5]2=[N:4][CH:3]=1.[F:13][C:14]1[CH:15]=[C:16]([C:29]2[C:30]([C:35]#[N:36])=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:17]=[C:18](B2OC(C)(C)C(C)(C)O2)[CH:19]=1>>[F:13][C:14]1[CH:15]=[C:16]([C:29]2[C:30]([C:35]#[N:36])=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:17]=[C:18]([C:2]2[N:6]3[CH:7]=[CH:8][C:9]([CH2:11][OH:12])=[N:10][C:5]3=[N:4][CH:3]=2)[CH:19]=1

Participants

3

Reactant 2

HCID 116742013'-Fluoro-5'-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrileHCID 180012743-Bromoimidazo[1,2-a]pyrimidin-7-ylmethanol

Product 1

HCID 101322443'-Fluoro-5'-(7-hydroxymethylimidazo[1,2-alpha]pyrimidin-3-yl)biphenyl-2-carbonitrile

Procedure

3-Bromoimidazo[1,2-α]pyrimidin-7-ylmethanol was coupled with 3′-fluoro-5′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile as described in Example 1 to give 3′-fluoro-5′-(7-hydroxymethylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile as a yellow solid: δH (360 MHz, DMSO) 4.71 (2H, d, J 6), 5.81 (1H, t, J 6), 7.31 (1H, d, J 7), 7.63 (1H, d, J 9), 7.74-7.95 (5H, m), 8.10 (1H, d, J 8), 8.14 (1H, s), 9.26 (1H, d, J 7); m/z (ES+) 345 (M++H).

Sources & evidence

ORD record
ord-50532869c3f3488f992fd042493de0d7
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

Loading…