4'-(Trifluoromethyl)(1,1'-biphenyl)-2-carboxylic acid → ethyl 1-ethyl-5-({2-[4-(trifluoromethyl)phenyl]benzene}amido)-1H-indole-2-carboxylate

HRID 489989Notes

Reaction equation

HRID 489989 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:15]([OH:17])=O)=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.[CH2:20]([O:22][C:23]([C:25]1[N:26]([CH2:37][CH3:38])[C:27]2[C:32]([CH:33]=1)=[CH:31][C:30]([N+:34]([O-])=O)=[CH:29][CH:28]=2)=[O:24])[CH3:21].CCN(C(C)C)C(C)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH2:20]([O:22][C:23]([C:25]1[N:26]([CH2:37][CH3:38])[C:27]2[C:32]([CH:33]=1)=[CH:31][C:30]([NH:34][C:15]([C:10]1[C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:19])[F:18])=[CH:8][CH:7]=3)=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:17])=[CH:29][CH:28]=2)=[O:24])[CH3:21]

Participants

6

Reactant 4

HCID 552514'-(Trifluoromethyl)(1,1'-biphenyl)-2-carboxylic acidHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 12148796ethyl 1-ethyl-5-nitro-1H-indole-2-carboxylate

Product 1

HCID 12148798ethyl 1-ethyl-5-({2-[4-(trifluoromethyl)phenyl]benzene}amido)-1H-indole-2-carboxylateYield 54.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4′-Trifluoromethyl-biphenyl-2-carboxylic acid (5.04 g, 18.95 mmol) and 1-ethyl-5-nitro-1H-indole-2-carboxylic acid ethyl ester (4.00 g, 17.23 mmol) were dissolved in DCM (100 mL). DIEA (8 g, 61.8 mmol) was added to the above mixture and the mixture was stirred at room temperature for 5 minutes. PyBroP (9.63 g, 20.67 mmol) was added to the above solution in one portion. The reaction mixture was stirred for another 3 hours. The precipitate was filtered off and washed with cold DCM to provide the title compound (4.5 g, 54.4%).

Workup

  1. stirringThe reaction mixture was stirred for another 3 hours
  2. filtrationThe precipitate was filtered off
  3. washwashed with cold DCM

Sources & evidence

ORD record
ord-c736b50410fb4dd29640ffaea75fd593
Source dataset
uspto-grants-2005_12
Patent number
US06979692B2

Reaction notes

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