Diisopropylethylamine → 4-(3-Fluorobenzyl)-N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)benzamide

HRID 1777669Notes

Reaction equation

HRID 1777669 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.[NH2:19][CH2:20][CH2:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([OH:31])[CH:29]=2)[NH:24][CH:23]=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>[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]([NH:19][CH2:20][CH2:21][C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[C:28]([OH:31])[CH:29]=3)[NH:24][CH:23]=2)=[O:12])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 160436Serotonin 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 679741324-(3-Fluorobenzyl)-N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)benzamideYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(3-Fluorobenzyl)-N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)benzamide was prepared according to method A with the 4-(3-fluorobenzyl)benzoic acid (0.080 g, 0.347 mmol), 3-(2-aminoethyl)-1H-indol-5-ol hydrochloride (0.081 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 0.093 g (67%) of the title compound as a white solid.

Workup

  1. custom4-(3-Fluorobenzyl)-N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)benzamide was prepared

Sources & evidence

ORD record
ord-2b78dc40068b4a41a97b2217397256aa
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

Loading…