Methanol → HCID 59762370, compound

HRID 40151Notes

Reaction equation

HRID 40151 reaction equation
[CH3:1][O-:2].[Na+].[Na].CO.[CH2:7]([N:14]1[C:22]2[C:17](=[CH:18][C:19]([F:24])=[C:20](I)[CH:21]=2)[C:16]([C:25]([NH:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[C:31]([F:36])[CH:30]=2)=[O:26])=[C:15]1[CH:37]([CH3:39])[CH3:38])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CN(C=O)C.[Cu]I>[CH2:7]([N:14]1[C:22]2[C:17](=[CH:18][C:19]([F:24])=[C:20]([O:2][CH3:1])[CH:21]=2)[C:16]([C:25]([NH:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[C:31]([F:36])[CH:30]=2)=[O:26])=[C:15]1[CH:37]([CH3:39])[CH3:38])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 69228284HCID 69228284, compound2×

Product 1

HCID 59762370HCID 59762370, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of sodium methoxide (freshly prepared from 25 mg sodium and 1 ml MeOH) and CuI (30 mg, 0.16 mmol) was added a solution of 1-benzyl-N-(3,4-difluorobenzyl)-5-fluoro-6-iodo-2-isopropyl-1H-indole-3-carboxamide (Compound 179, 30 mg, 0.053 mmol) in DMF (0.5 ml). The reaction was heated to 110 ° C. for 16 h, and was filtered and concentrated. The residue was purified by chromatography on silica gel (0→30% EtOAc-hexanes) to yield the title compound.

Workup

  1. filtrationwas filtered
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography on silica gel (0→30% EtOAc-hexanes)

Sources & evidence

ORD record
ord-b33bc589171a450598d985c36067eb3b
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Reaction notes

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