1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → 6-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)pyridin-3-amine

HRID 2060721Notes

Reaction equation

HRID 2060721 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[N:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:16][N:17]1[CH:21]=[C:20](B2OC(C)(C)C(C)(C)O2)[CH:19]=[N:18]1>>[CH3:16][N:17]1[CH:21]=[C:20]([C:2]2[CH:7]=[C:6]([O:8][C:9]3[N:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=3)[CH:5]=[CH:4][N:3]=2)[CH:19]=[N:18]1

Participants

3

Reactant 2

HCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 866416916-(2-Chloropyridin-4-yloxy)pyridin-3-amine

Product 1

HCID 673969346-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)pyridin-3-amineYield 64%

Procedure

Using a procedure analogous to Example A13, 6-(2-chloropyridin-4-yloxy)pyridin-3-amine (6.06 g, 27.3 mmol) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (8.53 g, 41.0 mmol) were combined to provide 6-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)pyridin-3-amine (4.67 g, 64% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.3 (m, 1H), 8.2 (s, 1H), 7.98 (s, 1H), 7.65 (s, 1H), 7.3 (s, 1H), 7.25-7.2 (m, 1H), 6.85-6.81 (m, 1H), 6.6-6.55 (m, 1H), 5.3 (s, 2H), 3.8 (s, 3H); MS (ESI) m/z: 268.1 (M+H+).

Sources & evidence

ORD record
ord-a38ffaea3dd1400ebcc90074f1688c66
Source dataset
uspto-grants-2012_10
Patent number
US08278331B2

Reaction notes

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