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

HRID 2183869Notes

Reaction equation

Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]([O:15][CH3:16])([O:13][CH3:14])[CH3:12])=[N:10][C:5]2=[N:4][CH:3]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21](B2OC(C)(C)C(C)(C)O2)=[CH:20][C:19]=1[C:33]1[C:34]([C:39]#[N:40])=[CH:35][CH:36]=[CH:37][CH:38]=1>>[CH3:14][O:13][C:11]([C:9]1[CH:8]=[CH:7][N:6]2[C:2]([C:21]3[CH:22]=[CH:23][C:18]([F:17])=[C:19]([C:33]4[C:34]([C:39]#[N:40])=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH:20]=3)=[CH:3][N:4]=[C:5]2[N:10]=1)([O:15][CH3:16])[CH3:12]

Participants

Reactant 2

HCID 117716472′-Fluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-2-carbonitrile

HCID 180012923-Bromo-7-(1,1-dimethoxyethyl)imidazo[1,2-a]pyrimidine

Product 1

HCID 697089515'-[7-(1,1-Dimethoxyethyl)imidazo[1,2-alpha]pyrimidin-3-yl]-2'-fluorobiphenyl-2-carbonitrileYield 100.2%

Procedure

3-Bromo-7-(1,1-dimethoxyethyl)imidazo[1,2-α]pyrimidine (860 mg, 3 mmol) was coupled with 2′-fluoro-5′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile (1.45 g, 4.5 mmol) as described in Example 1 to give crude 5′-[7-(1,1-dimethoxyethyl)imidazo[1,2-α]pyrimidin-3-yl]-2′-fluorobiphenyl-2-carbonitrile (1.21 g).

Sources & evidence

ORD record: ord-f91e617b7fc8429d93911be8103f1e49
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06900215B2

Reaction notes

Loading…