Methyl iodide → HCID 71468219, compound

HRID 1401067Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To solution containing (E)-tert-butyl 3-(3-(2-(4-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 acetone (5.0 ml), iodomethane (0.0673 ml, 1.08 mmol) was added drop-by-drop at 0° C. The reaction mixture was refluxed at 60° C. for 72 hr. After concentration under reduced pressure, the solution was separated through silica gel chromatography (CHCl3:methanol=70:1) so that ivory solid form of (E)-tert-butyl 3-(3-(1-isopropyl-2-(4-methoxybenzoyl)hydrazinyl)-3-oxoprop-1-enyl)-1H-indole-1-carboxylate was obtained (38.4 mg, 37.2%).

Workup

concentrationAfter concentration under reduced pressure
customthe solution was separated through silica gel chromatography (CHCl3:methanol=70:1) so that ivory solid form of (E)-tert-butyl 3-(3-(1-isopropyl-2-(4-methoxybenzoyl)hydrazinyl)-3-oxoprop-1-enyl)-1H-indole-1-carboxylate
customwas obtained (38.4 mg, 37.2%)

Sources & evidence

ORD record: ord-7ba0e02b6572440d913048c766ade274
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906952B2

Reaction notes

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