Cesium fluoride → 3-(1,3-benzoxazol-2-yl)-5-(3,5-dimethyl-1H-pyrazol-4-yl)pyridin-2-amine

HRID 908406Notes

Reaction equation

[F-].[Cs+].[O:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[C:12]1[C:13]([NH2:19])=[N:14][CH:15]=[C:16](Br)[CH:17]=1.[CH3:20][C:21]1[C:25](B2OC(C)(C)C(C)(C)O2)=[C:24]([CH3:35])[NH:23][N:22]=1>CO.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[O:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[C:12]1[C:13]([NH2:19])=[N:14][CH:15]=[C:16]([C:25]2[C:21]([CH3:20])=[N:22][NH:23][C:24]=2[CH3:35])[CH:17]=1

Participants

Conditions

Temperature: 140 °C

Procedure

Bis(triphenylphosphine) palladium (II) chloride (85 mg) and caesium fluoride (1.1 g) were added to a degassed solution of 3-(1,3-benzoxazol-2-yl)-5-bromo-pyridin-2-amine (700 mg) and 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (563 mg) in Methanol (14 ml). The suspension was stirred at 140° C. for 2 hours in a 300 W microwave. The mixture was adsorbed on silica gel and purified by flash chromatography on silica gel eluting with 5 to 10% methanol in dichloromethane. The solvent was evaporated to dryness to afford 3-(1,3-benzoxazol-2-yl)-5-(3,5-dimethyl-1H-pyrazol-4-yl)pyridin-2-amine (120 mg). NMR Spectrum: (DMSOd6) 2.22 (s, 6H), 7.40-7.487 (m, 2H), 7.66 (bs, 2H), 7.76-7.81 (m, 1H), 7.82-7.87 (m, 1H), 8.13 (d, 1H), 8.18 (d, 1H); Mass spectrum: M+H+ 306

Workup

custompurified by flash chromatography on silica gel eluting with 5 to 10% methanol in dichloromethane
customThe solvent was evaporated to dryness

Sources & evidence

ORD record: ord-5847a94767db410192667c6a21460e47
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017611B2

Reaction notes

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