3-(2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)pyridine → HCID 69709578, compound

HRID 2183998Notes

Reaction equation

HRID 2183998 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]3([CH3:18])[CH2:15][O:14][C:13]([CH3:17])([CH3:16])[O:12]3)=[N:10][C:5]2=[N:4][CH:3]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23](B2OC(C)(C)C(C)(C)O2)=[CH:22][C:21]=1[C:35]1[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=1>>[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[N:6]3[CH:7]=[CH:8][C:9]([C:11]4([CH3:18])[CH2:15][O:14][C:13]([CH3:17])([CH3:16])[O:12]4)=[N:10][C:5]3=[N:4][CH:3]=2)=[CH:22][C:21]=1[C:35]1[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=1

Participants

3

Reactant 2

HCID 114265233-(2-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)pyridineHCID 69707948HCID 69707948, compound

Product 1

HCID 69709578HCID 69709578, compound

Procedure

3-Bromo-7-(2,2,4-trimethyl-[1,3]dioxolan-4-yl)imidazo[1,2-α]pyrimidine was coupled with 3-[2-fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]pyridine as described in Example 65 to give 3-[4-fluoro-3-(pyridin-3-yl)phenyl]-7-(2,2,4-trimethyl-[1,3]dioxolan-4-yl)imidazo[1,2-α]pyrimidine as an orange oil: δH (400 MHz, d6-DMSO) 1.33 (3H, s), 1.47 (3H, s), 1.59 (3H, s), 4.08 (1H, d, J 9), 4.49 (1H, d, J 9), 7.31 (1H, d, J 7), 7.54-7.59 (2H, m), 7.77-7.81 (1H, m), 7.94 (1H, dd, J 7 and 2), 8.01 (1H, s), 8.09-8.12 (1H, m), 8.65 (1H, dd, J 5 and 2), 8.89 (1H, s), 9.08 (1H, d, J 7).

Sources & evidence

ORD record
ord-5f1e86acc6944d68b544e8c0b33aeef7
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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