Methyl iodide → HCID 71468218, compound

HRID 1401066Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][CH:34]=1)[C:5]([NH:7][N:8]([C:12](=[O:31])/[CH:13]=[CH:14]/[C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:16]=1)[CH:9]([CH3:11])[CH3:10])=[O:6].[C:35]([O-])([O-])=O.[K+].[K+].IC>C(#N)C>[CH:9]([N:8]([C:12](=[O:31])/[CH:13]=[CH:14]/[C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[CH:16]=1)[NH:7][C:5](=[O:6])[C:4]1[CH:32]=[CH:33][CH:34]=[C:2]([O:1][CH3:35])[CH:3]=1)([CH3:11])[CH3:10]

Participants

Conditions

Temperature: 85 °C

Procedure

To solution containing (E)-tert-butyl 3-(3-(2-(3-hydroxybenzoyl)-1-isopropylhydrazinyl)-3-oxoprop-1-enyl)-1H-indole-1-carboxylate (100 mg, 0.22 mmol) and K2CO3 (35.8 mg, 0.26 mmol) dissolved in anhydrous acetonitrile (10.0 ml), iodomethane (0.0673 ml, 1.08 mmol) was added drop-by-drop at 0° C. The reaction mixture was refluxed for 12 hr at 85° C. After concentration under reduced pressure, the solution was separated through the silica gel chromatography (30% EtOAc) so that ivoty solid form of (E)-tert-butyl 3-(3-(1-isopropyl-2-(3-methoxybenzoyl)hydrazinyl)-3-oxoprop-1-enyl)-1H-indole-1-carboxylate was obtained (43.5 mg, 42.2%).

Workup

concentrationAfter concentration under reduced pressure
customthe solution was separated through the silica gel chromatography (30% EtOAc) so that ivoty solid form of (E)-tert-butyl 3-(3-(1-isopropyl-2-(3-methoxybenzoyl)hydrazinyl)-3-oxoprop-1-enyl)-1H-indole-1-carboxylate
customwas obtained (43.5 mg, 42.2%)

Sources & evidence

ORD record: ord-885ceedb450345d882f0217995d9f444
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906952B2

Reaction notes

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