Phosphorus oxychloride → HCID 12985698, 화합물

반응식

[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:17])[C:13]=2[C:14](O)=O)[CH:5]=[CH:6][CH:7]=1.P(Cl)(Cl)([Cl:20])=O>>[Cl:20][C:14]1[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=2[N:8]=[C:9]2[CH:10]=[N:11][N:12]([CH3:17])[C:13]=12.[Cl:20][C:14]1[C:3]2[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=2[N:8]=[C:9]2[CH:10]=[N:11][N:12]([CH3:17])[C:13]=12

참가 물질

반응물 2

HCID 24813Phosphorus oxychloride

HCID 12985697HCID 12985697, 화합물

생성물 2

HCID 12985698HCID 12985698, 화합물수율 40%

HCID 12985699HCID 12985699, 화합물수율 24%

실험 절차

A mixture of 4-[(3-fluorophenyl)amino]-1-methyl-1H-pyrazole-5-carboxylic acid (EXAMPLE 3, step 1, 470 mg, 2.00 mmol) in phosphorus oxychloride (10 ml) was refluxed for 3 h. After cooling to room temperature, the mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate (100 ml), washed with water (30 ml) and saturated aqueous sodium bicarbonate (30 ml×2) and dried over magnesium sulfate. Removal of solvent gave a dark red residue, which was chromatographed on a column of silica gel eluting with ethyl acetate/hexane (1:5) to afford 189 mg (40%) of the 9-chloro-6-fluoro-1-methyl-1H-pyrazolo[4,3-b]quinoline as a pale yellow solid and 111 mg (24%) of the 9-chloro-8-fluoro-1-methyl-1H-pyrazolo[4,3-b]quinoline as a yellow solid.