Methyl morpholine oxide → 2-Acetyl-N-(3,4-difluorobenzyl)-6-isopropoxy-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide

HRID 40108Notes

Reaction equation

HRID 40108 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][C:34]=1[F:35])[CH2:5][NH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH:19]([CH3:21])[CH3:20])=[CH:15][CH:16]=2)[N:11]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[C:10]=1[CH:29]([OH:31])[CH3:30])=[O:8].C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[C:29]([C:10]1[N:11]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[C:12]2[C:17]([C:9]=1[C:7]([NH:6][CH2:5][C:4]1[CH:32]=[CH:33][C:34]([F:35])=[C:2]([F:1])[CH:3]=1)=[O:8])=[CH:16][CH:15]=[C:14]([O:18][CH:19]([CH3:21])[CH3:20])[CH:13]=2)(=[O:31])[CH3:30]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 59762339HCID 59762339, compound2×

Product 1

HCID 597623482-Acetyl-N-(3,4-difluorobenzyl)-6-isopropoxy-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(3,4-difluorobenzyl)-2-(1-hydroxyethyl)-6-isopropoxy-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide (Compound 108, 8.0 mg, 0.017 mmol) in CH2Cl2 (1 ml) was added NMO (6.0 mg, 0.051 mmol) and TPAP (0.6 mg, 0.0017 mmol). The reaction was stirred at room temperature for 1 h and was purified directly by PTLC (75% EtOAc-hexanes) to yield the title compound.

Workup

  1. customwas purified directly by PTLC (75% EtOAc-hexanes)

Sources & evidence

ORD record
ord-a62061fc31174a1087b623258c6d1993
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Reaction notes

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