Diisopropylethylamine → HCID 67974203, compound

HRID 1777690Notes

Reaction equation

HRID 1777690 reaction equation
Cl.[F: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:28]=[CH:27][C:23](C(O)=O)=[CH:22][CH:21]=1.CN([C:35]([O:39]N1N=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.ClCCl.C(OCC)(=O)C.CCCCCCC>[F: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:35](=[O:39])[C:27]1[CH:23]=[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:28]=1

Participants

9

Reactant 4

HCID 81531DiisopropylethylamineHCID 197774Indole, 3-(2-aminoethyl)-5-fluoro-, hydrochlorideHCID 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 67974203HCID 67974203, compoundYield 7.3%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×HCID 8900HeptaneSolvent

Procedure

N-(2-(5-Fluoro-1H-indol-3-yl)ethyl)-3-(3-fluorobenzyl)benzamide was prepared following Method A starting from 2-(5-fluoro-1H-indol-3-yl)ethanamine hydrochloride (0.060 g; 0.279 mmol), 4-(3-fluorobenzyl)benzoic acid (0.070 g; 0.307 mmol), HATU (0.127 g; 0.335 mmol) and N,N-diisopropylethylamine (0.120 mL; 0.698 mmol) in DMF (5 mL). Two flash chromatographies on silica gel eluting with 1 to 20% ethyl acetate in dichloromethane and 20 to 100% ethyl acetate in heptane furnished 0.008 g (7%) of the title compound as a white solid.

Workup

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

Sources & evidence

ORD record
ord-6c6d39d8fcec4b35b065c687ec4019bd
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

Loading…