2-Chlorobenzoyl chloride → HCID 59505228, compound
Reaction equation
[F:1][C:2]([F:19])([F:18])[CH2:3][NH:4][C@H:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=2)[CH2:7][CH2:6]1.[Cl:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24]>C(Cl)Cl>[Cl:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([N:4]([C@H:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=2)[CH2:7][CH2:6]1)[CH2:3][C:2]([F:18])([F:19])[F:1])=[O:24]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a cooled (0° C.) solution of (R)-methyl 3-(2,2,2-trifluoroethylamino)-2,3-dihydro-1H-indene-5-carboxylate (A-18) (870 mg, 3.18 mmol, 1.0 eq.) in methylene chloride (12 ml) was added TEA (1.1 ml, 7.95 mmol, 2.5 eq.) and the reaction mixture was allowed to stir for 15 min. 2-Chlorobenzoyl chloride (0.44 ml, 3.50 mmol, 1.1 eq) was added to the reaction mixture and it was stirred at RT for 1 h. After completion of the reaction (monitored by TLC), the mixture was diluted with methylene chloride (50 ml) and the organic layer was washed with water (20 ml) and brine (20 ml), and dried over anhydrous Na2SO4. The solvent was evaporated to afford the crude product which was purified by column chromatography (silica gel; 7% ethyl acetate/hexanes) to yield the desired compounds as a colourless gummy solid. Yield: 85% (1.1 g, 2.67 mmol).
Workup
- stirringwas stirred at RT for 1 h
- customAfter completion of the reaction (monitored by TLC)
- washthe organic layer was washed with water (20 ml) and brine (20 ml)
- dry with materialdried over anhydrous Na2SO4
- customThe solvent was evaporated
- customto afford the crude product which
- customwas purified by column chromatography (silica gel; 7% ethyl acetate/hexanes)
Sources & evidence
- ORD record
- ord-a90fe608806c4e40b97ba7fd310eea38
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08455475B2
Reaction notes
Loading…