Diisopropylethylamine → N-(2-(5-Chloro-1H-indol-3-yl)ethyl)-5-(3-fluorobenzyl)picolinamide

HRID 1777676Notes

Reaction equation

HRID 1777676 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][NH2:14].[F:15][C:16]1[CH:17]=[C:18]([CH:29]=[CH:30][CH:31]=1)[CH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:26](O)=[O:27])=[N:24][CH:25]=1.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:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][NH:14][C:26](=[O:27])[C:23]1[CH:22]=[CH:21][C:20]([CH2:19][C:18]2[CH:29]=[CH:30][CH:31]=[C:16]([F:15])[CH:17]=2)=[CH:25][N:24]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 679745615-(3-Fluorobenzyl)picolinic acid

Product 1

HCID 67974629N-(2-(5-Chloro-1H-indol-3-yl)ethyl)-5-(3-fluorobenzyl)picolinamideYield 23.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(2-(5-Chloro-1H-indol-3-yl)ethyl)-5-(3-fluorobenzyl)picolinamide was prepared according to Method A starting from 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.140 g; 0.605 mmol), 5-(3-fluorobenzyl)picolinic acid (0.139 g; 0.605 mmol), HATU (0.254 g; 0.668 mmol) and N,N-diisopropylethylamine (0.262 mL; 1.52 mmol) in DMF (5 mL). Flash chromatography on silica gel (eluent 20 to 100% ethyl acetate in heptane) furnished 0.057 g (23%) of the title compound as a white solid.

Workup

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

Sources & evidence

ORD record
ord-0217cf1032ac4c18a37d915a1bcd08bf
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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