Cesium carbonate → 3-(2-Chloro-5-(trifluoromethyl)pyridin-4-ylamino)-N-methylpicolinamide

HRID 1887695Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6](I)[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[NH2:13][C:14]1[C:15]([C:20]([NH:22][CH3:23])=[O:21])=[N:16][CH:17]=[CH:18][CH:19]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:1][C:2]1[CH:7]=[C:6]([NH:13][C:14]2[C:15]([C:20]([NH:22][CH3:23])=[O:21])=[N:16][CH:17]=[CH:18][CH:19]=2)[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

The mixture of 2-chloro-4-iodo-5-(trifluoromethyl)pyridine (0.615 g, 2.0 mmol, 1.0 eq), 3-amino-N-methylpicolinamide (0.303 g, 1.2 eq), Pd2(dba)3 (0.183 g, 0.1 eq), Xantphos (0.347 g, 0.3 eq), Cs2CO3 (1.3 g, 2.0 eq) in dioxane (15 mL) was stirred at 90° C. in an oil bath overnight. The mixture was cooled to room temperature and filtered through a celite pad. The celite pad was washed with methanol. The solvent was removed to obtain the crude which was purified by silica gel chromatography (20%˜80% EtOAc/Hex) to obtain the desired product (0.146 g, isolated yield 22%).

Workup

temperatureThe mixture was cooled to room temperature
filtrationfiltered through a celite pad
washThe celite pad was washed with methanol
customThe solvent was removed
customto obtain the crude which
customwas purified by silica gel chromatography (20%˜80% EtOAc/Hex)

Sources & evidence

ORD record: ord-9efa5772828a4054931c71134f4294d5
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501763B2

Reaction notes

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