Dimethylformamide → HCID 58015530, compound

HRID 219289

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([F:8])=[N:6][CH:7]=1.[CH3:9][C:10]1[CH:14]=[C:13]([Sn](CCCC)(CCCC)CCCC)[O:12][N:11]=1.C1CCC(P(C2C(C3C=CC=CC=3)=CC=CC=2)C2CCCCC2)CC1.CN(C=O)C>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]>[F:8][C:5]1[CH:4]=[CH:3][C:2]([C:13]2[O:12][N:11]=[C:10]([CH3:9])[CH:14]=2)=[CH:7][N:6]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A 48 mL tube was charged with 5-bromo-2-fluoropyridine (1.17 ml, 11.4 mmol), 3-methyl-5-(tributylstannyl)isoxazole (5.29 g, 14.2 mmol), cyclohexyl JohnPhos (0.398 g, 1.14 mmol), Pd2dba3 (0.312 g, 0.341 mmol), and DMF (12.4 ml, 159 mmol), flushed with argon, sealed, then heated at 90° C. for 16 hours. Additional 3-methyl-5-(tributylstannyl)isoxazole (5.29 g, 14.2 mmol) (2 g), Pd2 dba3 (0.312 g, 0.341 mmol), and cyclohexyl JohnPhos (0.398 g, 1.14 mmol) were added and the mixture was stirred at 90° C. for 10 more hours. This was concentrated and the brown residue was purified by MPLC, eluting with 15% ethyl acetate in hexanes isocratic. 2-fluoro-5-(3-methylisoxazol-5-yl)pyridine (1.1029 g, 54.5% yield) isolated as a light yellow solid.

Workup

customflushed with argon
customsealed
concentrationThis was concentrated
customthe brown residue was purified by MPLC
washeluting with 15% ethyl acetate in hexanes isocratic

Sources & evidence

ORD record: ord-05945d12f2a2422db148d935ab22bd5d
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198448B2

Linked notes

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