Sodium Carbonate → 3-fluoro-4-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)aniline

HRID 450413Notes

Reaction equation

HRID 450413 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][C:10]=2[F:16])[CH:5]=[CH:4][N:3]=1.[CH3:17][N:18]1[CH:22]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH:20]=[N:19]1.C([O-])([O-])=O.[Na+].[Na+]>>[F:16][C:10]1[CH:11]=[C:12]([CH:14]=[CH:15][C:9]=1[O:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:21]2[CH:20]=[N:19][N:18]([CH3:17])[CH:22]=2)[CH:7]=1)[NH2:13]

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 598529984-(2-Chloropyridin-4-yloxy)-3-fluorobenzenamine

Product 1

HCID 593227693-fluoro-4-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)anilineYield 34%

Procedure

Using a procedure analogous to Example A1, 4-(2-chloropyridin-4-yloxy)-3-fluoroaniline (3 g, 11.6 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (3.4 g, 16.4 mmol), Na2CO3 (2.7 g, 25.2 mmol) and Pd(Ph3)4 (1.5 g, 0.1 eq) were combined to give 3-fluoro-4-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)aniline (1.1 g, 34% yield). 1H NMR (400 MHz, DMSO-d6): δ (8.31 (d, J=5.6 Hz, 1H), 8.22 (s, 1H), 7.93 (s, 1H), 7.14 (s, 1H), 6.98 (m, 1H), 6.55-6.49 (m, 2H), 6.42 (d, J=7.2 Hz, 1H), 5.44 (s, 2H), 3.86 (s, 3H); MS (ESI) m/z: (M+H+): 285.2.

Sources & evidence

ORD record
ord-a6e6b1be71fc49eea876bad6dad7eba3
Source dataset
uspto-grants-2013_07
Patent number
US08486951B2

Reaction notes

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