Trifluoroacetic acid → HCID 57963067, compound

HRID 1403249Notes

Reaction equation

[F:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[F:9][C:10]1[CH:11]=[C:12]([CH:18]=O)[CH:13]=[N:14][C:15]=1[O:16][CH3:17].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(#N)C>[F:9][C:10]1[CH:11]=[C:12]([CH2:18][NH:8][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[N:7]=2)[CH:13]=[N:14][C:15]=1[O:16][CH3:17]

Participants

Conditions

Temperature: 80 °C

Procedure

To 6-fluoro-pyridin-2-ylamine (14, 1.50 g, 13.4 mmol) in 52.9 mL of acetonitrile, 5-fluoro-6-methoxy-pyridine-3-carbaldehyde (23, 2.00 g, 12.9 mmol), triethylsilane (10.6 mL, 66.3 mmol), and trifluoroacetic acid (5.3 mL, 69.0 mmol) were added. The reaction was stirred at 80° C. overnight, then concentrated under vacuum, combined with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography, eluting with 15-100% ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound as white solid (24, 3.21 g).

Workup

concentrationconcentrated under vacuum
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationthe filtrate concentrated under vacuum
customThe resulting material was purified by silica gel column chromatography
washeluting with 15-100% ethyl acetate in hexane
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-02019b8b1ed2485ab786287cb6ff2e7f
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912204B2

Reaction notes

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