Diisopropylethylamine → (S)-Methyl 1-(4-((5-((1-(3-bromophenyl)ethyl)carbamoyl)-2,3-dimethyl-1H-indol-1-yl)methyl)phenyl)cyclopropanecarboxylate

HRID 2170622Notes

Reaction equation

HRID 2170622 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:8]2[CH:28]=[CH:27][C:11]([CH2:12][N:13]3[C:21]4[C:16](=[CH:17][C:18]([C:22](O)=[O:23])=[CH:19][CH:20]=4)[C:15]([CH3:25])=[C:14]3[CH3:26])=[CH:10][CH:9]=2)[CH2:7][CH2:6]1)=[O:4].[Br:29][C:30]1[CH:31]=[C:32]([C@@H:36]([NH2:38])[CH3:37])[CH:33]=[CH:34][CH:35]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[Br:29][C:30]1[CH:31]=[C:32]([C@@H:36]([NH:38][C:22]([C:18]2[CH:17]=[C:16]3[C:21](=[CH:20][CH:19]=2)[N:13]([CH2:12][C:11]2[CH:27]=[CH:28][C:8]([C:5]4([C:3]([O:2][CH3:1])=[O:4])[CH2:7][CH2:6]4)=[CH:9][CH:10]=2)[C:14]([CH3:26])=[C:15]3[CH3:25])=[O:23])[CH3:37])[CH:33]=[CH:34][CH:35]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9952938(S)-1-(3-bromophenyl)ethanamineHCID 710757301-(4-(1-(Methoxycarbonyl)cyclopropyl)benzyl)-2,3-dimethyl-1H-indole-5-carboxylic acid

Product 1

HCID 71075315(S)-Methyl 1-(4-((5-((1-(3-bromophenyl)ethyl)carbamoyl)-2,3-dimethyl-1H-indol-1-yl)methyl)phenyl)cyclopropanecarboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(4-(1-(methoxycarbonyl)cyclopropyl)benzyl)-2,3-dimethyl-1H-indole-5-carboxylic acid (50 mg, 0.13 mmol) in DMF (1 mL) was added (S)-1-(3-bromophenyl)ethylamine (21 μL), DIEA (45 μL) and HATU (54 mg). The reaction mixture was allowed to stir at rt for 30 min, and then was diluted by ethyl acetate. The resulting mixture was washed with a 0.5 N HCl solution, a saturated solution of NaHCO3, and brine, dried on MgSO4, and concentrated to afford a yellow oil (73 mg) which was directly used without further purification.

Workup

  1. washThe resulting mixture was washed with a 0.5 N HCl solution
  2. dry with materiala saturated solution of NaHCO3, and brine, dried on MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c9aa63ac8fc24b15905eeac35ef2a093
Source dataset
uspto-grants-2015_06
Patent number
US09051265B2

Reaction notes

Loading…