5-Methoxytryptamine → HCID 67974597, compound

HRID 1777657Notes

Reaction equation

HRID 1777657 reaction equation
[CH3:1][O: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]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23](O)=[O:24].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>[F:15][C:16]1[CH:17]=[C:18]([CH:29]=[CH:30][CH:31]=1)[CH2:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23]([NH:14][CH2:13][CH2:12][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)[NH:8][CH:7]=1)=[O:24]

Participants

6

Reactant 4

HCID 18335-MethoxytryptamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67974126HCID 67974126, compound

Product 1

HCID 67974597HCID 67974597, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(3-Fluorobenzyl)-N-(2-(5-methoxy-1H-indol-3-yl)ethyl)benzamide was prepared according to method A with 2-(5-methoxy-1H-indol-3-yl)ethanamine (0.060 g; 0.315 mmol), 3-(3-fluorobenzyl)benzoic acid (0.073 g; 0.316 mmol), HATU (0.120 g; 0.316 mmol) and N,N-diisopropylethylamine (0.135 mL; 0.788 mmol) in DMF (5 mL). Flash chromatography on silica gel (eluent 1 to 20% ethyl acetate in dichloromethane) furnished 0.065 g (51%) of the title compound as a white solid.

Workup

  1. custom3-(3-Fluorobenzyl)-N-(2-(5-methoxy-1H-indol-3-yl)ethyl)benzamide was prepared

Sources & evidence

ORD record
ord-7dd83b53b07045e5a16f46a2a68f8904
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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