4-Bromoaniline → (R)-N-(4-bromophenyl)-2-(1,1,1-trifluoro-2-methylpropan-2-yl)-5,6,7,8-tetrahydroquinoline-6-carboxamide
Reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([C:6]1[CH:15]=[CH:14][C:13]2[CH2:12][C@H:11]([C:16]([OH:18])=O)[CH2:10][CH2:9][C:8]=2[N:7]=1)([CH3:5])[CH3:4].[Br:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1.C(N(CC)CC)C>O1CCOCC1>[Br:21][C:22]1[CH:28]=[CH:27][C:25]([NH:26][C:16]([C@@H:11]2[CH2:10][CH2:9][C:8]3[N:7]=[C:6]([C:3]([CH3:5])([CH3:4])[C:2]([F:19])([F:1])[F:20])[CH:15]=[CH:14][C:13]=3[CH2:12]2)=[O:18])=[CH:24][CH:23]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 14 °C
Procedure
(R)-2-(1,1,1-Trifluoro-2-methylpropan-2-yl)-5,6,7,8-tetrahydroquinoline-6-carboxylic acid (30 mg), 4-bromoaniline (17.9 mg), propanephosphonic acid cyclic anhydride (50% wt solution in dichloroethane) (0.093 mL), triethylamine (0.044 mL), and dioxane (2 mL) were combined and heated in a microwave at 14° C. for 20 mins. The solution was evaporated and the residue dissolved in ethyl acetate and extracted with sodium carbonate soln (2×20 ml) and brine (3×20 ml). The organic layer was separated, dried (Na2SO4), filtered and evaporated to give a gum which solidified on standing. Yield 40 mg.
Workup
- customThe solution was evaporated
- dissolutionthe residue dissolved in ethyl acetate
- extractionextracted with sodium carbonate soln (2×20 ml) and brine (3×20 ml)
- customThe organic layer was separated
- dry with materialdried (Na2SO4)
- filtrationfiltered
- customevaporated
- customto give a gum which
Sources & evidence
- ORD record
- ord-5bc795568cb3432e8e220c218a71fc21
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08153651B2
Reaction notes
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