Methanol → 3-[1-(3,5-Dimethyl-1h-pyrrol-2-yl)-meth-(z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid methyl ester

HRID 1826998Notes

Reaction equation

HRID 1826998 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][C:3]=1/[CH:8]=[C:9]1\[C:10](=[O:25])[N:11]([C:18](N2C=CN=C2)=[O:19])[C:12]2[C:17]\1=[CH:16][CH:15]=[CH:14][CH:13]=2.[CH3:26][OH:27]>>[CH3:26][O:27][C:18]([N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)/[C:9](=[CH:8]/[C:3]2[NH:4][C:5]([CH3:7])=[CH:6][C:2]=2[CH3:1])/[C:10]1=[O:25])=[O:19]

Participants

3

Reactant 2

HCID 887MethanolHCID 601112313-[1-(3,5-Dimethyl-1h-pyrrol-2-yl)-meth-(z)-ylidene]-1-(imidazol-1-ylcarbonyl)-1,3-dihydro-indol-2-one

Product 1

HCID 601112233-[1-(3,5-Dimethyl-1h-pyrrol-2-yl)-meth-(z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid methyl esterYield 63%

Procedure

A reaction mixture of 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-1-(imidazole-1-ylcarbonyl)-1,3-dihydro-indol-2-one (5.3 mg, 0.016 mmol) in 1.0 mL of methanol was stirred at room temperature for 64 h and filtered. The red solid was washed with methanol and dried in a vacuum oven overnight to afford 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid methyl ester (3.0 mg, 63%) as a red solid. 1H NMR (400 MHz, DMSO-d6) d 12.63 (s, 1H, NH-1′), 7.84–7.86 (m, 1H), 7.69 (s, 1H, H-vinyl), 7.56–7.68 (m, 1H), 7.19–7.22 (m, 2H), 6.06 (d, J=2.34 Hz, 1H, H-4′), 4.08 (s, 3H, OCH3), 2.40 (s, 3H, CH3), and 2.36 (s, 3H, CH3). MS m/z (relative intensity, %) 297 (100, [M+1]+.)

Workup

  1. filtrationfiltered
  2. washThe red solid was washed with methanol
  3. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-96b74cd844cf469784a0f4137eea7ccc
Source dataset
uspto-grants-2006_05
Patent number
US07053114B2

Reaction notes

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