1-(2-Methoxyethyl)-1H-pyrazole-4-boronic acid, pinacol ester → 2-Amino-N-(3-chloro-pyridin-4-yl)-5-[1-(2-methoxy-ethyl-)-1H-pyrazol-4-yl]nicotinamide

HRID 919238Notes

Reaction equation

HRID 919238 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[Cl:17])=[O:9])=[CH:6][C:5](Br)=[CH:4][N:3]=1.[CH3:19][O:20][CH2:21][CH2:22][N:23]1[CH:27]=[C:26](B2OC(C)(C)C(C)(C)O2)[CH:25]=[N:24]1>>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:26]2[CH:25]=[N:24][N:23]([CH2:22][CH2:21][O:20][CH3:19])[CH:27]=2)=[CH:6][C:7]=1[C:8]([NH:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][C:12]=1[Cl:17])=[O:9]

Participants

3

Reactant 2

HCID 112304911-(2-Methoxyethyl)-1H-pyrazole-4-boronic acid, pinacol esterHCID 710608052-amino-5-bromo-N-(3-chloro-4-pyridyl)pyridine-3-carboxamide

Product 1

HCID 710624762-Amino-N-(3-chloro-pyridin-4-yl)-5-[1-(2-methoxy-ethyl-)-1H-pyrazol-4-yl]nicotinamide

Procedure

Reaction of 2-amino-5-bromo-N-(3-chloro-4-pyridyl)pyridine-3-carboxamide with 1-(2-methoxy-ethyl)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole gives the compound “A38”; HPLC/MS: 1.39 min, [M+H]=373;

Workup

  1. customgives the compound “A38”
  2. custom1.39 min, [M+H]=373

Sources & evidence

ORD record
ord-b5f0cf001ea24f2db97e303194263a7b
Source dataset
uspto-grants-2016_03
Patent number
US09273029B2

Reaction notes

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