3-(2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)pyridine → HCID 10155078, compound

HRID 2183904Notes

Reaction equation

HRID 2183904 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[CH3:12])=[N:10][C:5]2=[N:4][CH:3]=1.[F:15][C:16]1[CH:21]=[CH:20][C:19](B2OC(C)(C)C(C)(C)O2)=[CH:18][C:17]=1[C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1>>[F:13][C:11]([C:9]1[CH:8]=[CH:7][N:6]2[C:2]([C:19]3[CH:20]=[CH:21][C:16]([F:15])=[C:17]([C:31]4[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=4)[CH:18]=3)=[CH:3][N:4]=[C:5]2[N:10]=1)([F:14])[CH3:12]

Participants

3

Reactant 2

HCID 114265233-(2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)pyridineHCID 69709942HCID 69709942, compound

Product 1

HCID 10155078HCID 10155078, compound

Procedure

3-Bromo-7-(1,1-difluoroethyl)imidazo[1,2-α]pyrimidine (113 mg, 0.43 mmol) was coupled with 3-[2-fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]pyridine as described in Example 1 to give 7-(1,1-difluoroethyl)-3-[4-fluoro-3-(pyridin-3-yl)phenyl]imidazo[1,2-α]pyrimidine as a white powder: δH (360 MHz, DMSO) 2.11 (3H, t, J 7), 7.36 (1H, d, J 7), 7.55-7.64 (2H, m), 7.83-7.87 (1H, m), 7.99-8.01 (1H, m), 8.11-8.13 (1H, m), 8.21 (1H, s), 8.66 (1H, dd, J 5 and 1), 8.91 (1H, s), 9.27 (1H, d, J 7).

Sources & evidence

ORD record
ord-1a6f0f0fcc4c4031bb22bd401f5068c8
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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