Trifluoroacetic acid → 7-(5-Dicyclopropylmethyl-thiazol-2-ylsulfanyl)-1-phenyl-[1,2,4]triazolo[4,3-a]quinoline
Reaction equation
[CH:1]1([C:4]([CH:31]2[CH2:33][CH2:32]2)([C:6]2[S:10][C:9]([S:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]3[C:22]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)=[N:23][N:24]=[C:17]3[CH:16]=[CH:15]4)=[N:8][CH:7]=2)O)[CH2:3][CH2:2]1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:31]1([CH:4]([CH:1]2[CH2:2][CH2:3]2)[C:6]2[S:10][C:9]([S:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]3[C:22]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)=[N:23][N:24]=[C:17]3[CH:16]=[CH:15]4)=[N:8][CH:7]=2)[CH2:33][CH2:32]1Participants
5
Procedure
To 10g (23 mg, 0.05 mmol) in CH2Cl2 (3 mL) was added triethylsilane (0.04 mL, 0.24 mmol) and TFA (0.04 mL, 0.49 mmol) at 0° C. After 4 hours at room temperature, additional triethylsilane (0.02 mL, 0.12 mmol) and TFA (0.02 mL, 0.25 mmol) as added at 0° C., and the reaction was stirred for another 3 hours at room temperature. The reaction was washed with saturated aqueous NaHCO3, and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated. The crude material was purified by silica gel chromatography to give the desired product, 10h.
Workup
- washThe reaction was washed with saturated aqueous NaHCO3
- extractionthe aqueous layer was extracted with EtOAc
- dry with materialThe combined organic layers were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe crude material was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-25bb40e01afc4efeb523a260b96ce07f
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07919621B2
Reaction notes
Loading…