Triphenylphosphine → HCID 117988751, compound

HRID 2201371Notes

Reaction equation

[CH2:1]([S:3][C:4]1[N:23]=[CH:22][CH:21]=[CH:20][C:5]=1[C:6]([NH:8][C:9]1[C:10]([OH:19])=[N:11][CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1)=O)[CH3:2].N(C(OCCOC)=O)=NC(OCCOC)=O.COCCOC(/N=N/C(OCCOC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl-].[NH4+]>C1COCC1>[CH2:1]([S:3][C:4]1[C:5]([C:6]2[O:19][C:10]3[C:9]([N:8]=2)=[CH:14][C:13]([C:15]([F:18])([F:17])[F:16])=[CH:12][N:11]=3)=[CH:20][CH:21]=[CH:22][N:23]=1)[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 0.69 g of 2-ethylsulfanyl-N-(2-hydroxy-5-trifluoromethylpyridin-3-yl) nicotinamide, 0.75 g of bis(2-methoxyethyl) azodicarboxylate (hereinafter referred to as DMEAD), 0.79 g of triphenylphosphine and 7 ml of THF was stirred at 50° C. for 4 hours. A saturated aqueous ammonium chloride solution was poured to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, then dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 0.34 g of 2-(2-ethylsulfanylpyridin-3-yl)-6-(trifluoromethyl)oxazolo[5,4-b]pyridine (hereinafter, referred to as Compound of Present Invention 32).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with water
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-73c58ee2016e4528b1d5c440db721d24
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09364000B2

Reaction notes

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