Cesium carbonate → HCID 66679827, compound

HRID 1842573Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10](I)=[N:9]2)=[N:6][CH:7]=1.[CH3:19][C:20]1[S:21][CH:22]=[CH:23][N:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].C([O-])(O)=O.[Na+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]([C:22]3[S:21][C:20]([CH3:19])=[N:24][CH:23]=3)=[N:9]2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of ethyl 1-(5-fluoropyridin-2-yl)-3-iodo-1H-pyrazole-4-carboxylate (0.40 g, 1.11 mmol) in DMF (3.7 mL) were added 2-methyl-1,3-thiazole (0.17 g, 1.66 mmol), palladium(II) acetate (25.0 mg, 0.11 mmol), triphenylphosphine (58.0 mg, 0.22 mmol) and cesium carbonate (0.72 g, 2.22 mmol). The mixture was heated 140° C. in a seal vial. After 2 h, water and saturated aqueous NaHCO3 were added and the mixture was extracted with ethyl acetate (3×). The combined organic extracts was dried over MgSO4, filtered and concentrated. Purification by silica gel chromatography (100% hexanes 50% hexanes/ethyl acetate) gave the title compound (0.24 g). MS 333.1 (M+1).

Workup

extractionthe mixture was extracted with ethyl acetate (3×)
dry with materialThe combined organic extracts was dried over MgSO4
filtrationfiltered
concentrationconcentrated
customPurification by silica gel chromatography (100% hexanes 50% hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-a4f13c0f1b9245bc927ff1c779eb8e83
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946231B2

Reaction notes

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