Diisopropylethylamine → HCID 67974639, compound

HRID 1777670Notes

Reaction equation

HRID 1777670 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=1.[Cl:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[N:24]([CH3:28])[CH:23]=[C:22]2[CH2:29][CH2:30][NH2:31].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[Cl:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[N:24]([CH3:28])[CH:23]=[C:22]2[CH2:29][CH2:30][NH:31][C:10](=[O:12])[C:9]1[CH:8]=[CH:7][C:6]([CH2:5][C:4]2[CH:15]=[CH:16][CH:17]=[C:2]([F:1])[CH:3]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 64876102-(5-Chloro-1-methyl-1H-indol-3-yl)-ethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 679746154-(3-Fluoro-benzyl)-benzoic acid

Product 1

HCID 67974639HCID 67974639, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(2-(5-Chloro-1-methyl-1H-indol-3-yl)ethyl)-4-(3-fluorobenzyl)benzamide was prepared according to method A with 4-(3-fluorobenzyl)benzoic acid (0.080 g, 0.347 mmol), 2-(5-chloro-1-methyl-1H-indol-3-yl)ethanamine (0.080 g; 0.382 mmol), HATU (0.145 g; 0.382 mmol) and N,N-diisopropylethylamine (0.150 mL; 0.869 mmol) in DMF (3 mL). Flash chromatography on silica gel (eluent 20 to 100% ethyl acetate in heptane) furnished 0.034 g (23%) of the title compound as a yellow oil.

Workup

  1. customN-(2-(5-Chloro-1-methyl-1H-indol-3-yl)ethyl)-4-(3-fluorobenzyl)benzamide was prepared

Sources & evidence

ORD record
ord-dd6f1586c43f475ea256fd145f10337b
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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