1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 86714335, compound

HRID 2200760Notes

Reaction equation

HRID 2200760 reaction equation
Br[C:2]1[C:3]([Cl:10])=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[CH3:11][N:12]1[CH:16]=[C:15](B2OC(C)(C)C(C)(C)O2)[CH:14]=[N:13]1>>[Cl:10][C:3]1[C:2]([C:15]2[CH:14]=[N:13][N:12]([CH3:11])[CH:16]=2)=[CH:7][N:6]=[C:5]([O:8][CH3:9])[CH:4]=1

Participants

3

Reactant 2

HCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 231336495-Bromo-4-chloro-2-methoxypyridine

Product 1

HCID 86714335HCID 86714335, compound

Procedure

Alternative way to prepare Compound 543: first, 5-bromo-4-chloro-2-methoxypyridine was reacted with 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole under the standard Suzuki-Coupling condition to form 4-chloro-2-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridine; then it was subject to HBr hydrolysis, followed by a second Suzuki-Coupling with (4-ethoxy-2-methylphenyl)boronic acid, then reaction with BnNH2 as described herein. Hydrogen chloride salt: 1H NMR (DMSO-d6, 400 MHz) 1H NMR (DMSO-d6, 400 MHz) δ 8.01 (s, 1H), 7.64 (s, 1H), 7.46 (s, 1H), 7.41-7.35 (m, 5H), 7.28 (m, 1H), 7.18 (d, J=8.8 Hz, 1H), 6.93 (s, 1H), 6.83 (d, J=8.8 Hz, 1H), 5.87 (s, 1H), 4.45 (s, 2H), 4.04 (q, J=6.8 Hz, 2H), 3.89 (s, 3H), 2.00 (s, 3H), 1.32 (t, J=6.8 Hz, 3H).

Sources & evidence

ORD record
ord-847875234ad045a29389b772d5c9beaf
Source dataset
uspto-grants-2016_06
Patent number
US09359379B2

Reaction notes

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