Dimethylformamide → n-((5-Chloro-1h-indol-3-yl)methyl)-5-(3-fluorobenzyl)isoxazole-3-carboxamide

HRID 58683Notes

Reaction equation

HRID 58683 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][NH2:12].CN(C([O:20][N:21]1N=N[C:23]2[CH:24]=[CH:25][CH:26]=N[C:22]1=2)=[N+](C)C)C.[F:30][P-](F)(F)(F)(F)F.C(N(CC)[CH:41]([CH3:43])[CH3:42])(C)C.C(O[CH2:50][CH3:51])(=O)C.CN([CH:55]=[O:56])C>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][NH:12][C:55]([C:22]1[CH:23]=[C:24]([CH2:25][C:26]2[CH:42]=[CH:41][CH:43]=[C:50]([F:30])[CH:51]=2)[O:20][N:21]=1)=[O:56]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21281458(5-Chloro-1H-indol-3-yl)methanamine

Product 1

HCID 66831683n-((5-Chloro-1h-indol-3-yl)methyl)-5-(3-fluorobenzyl)isoxazole-3-carboxamideYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound was prepared following Method A starting from (5-chloro-1H-indol-3-yl)methanamine (0.060 g; 0.332 mmol), the intermediate 11 (0.081 g; 0.365 mmol), HATU (0.139 g; 0.365 mmol) and N,N-diisopropylethylamine (0.075 mL; 0.432 mmol) in DMF (5 mL). Flash chromatography on silica gel eluting with 2 to 10% of ethyl acetate in dichloromethane afforded 0.028 g (22%) of N-((5-chloro-1H-indol-3-yl)methyl)-5-(3-fluorobenzyl)isoxazole-3-carboxamide as a solid.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-a3987e0d68e241ce850cd402def5523c
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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