Methyl chloroglyoxylate → methyl (1-methyl-6-morpholin-4-yl-1H-indol-3-yl)glyoxylate

HRID 651763Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[CH:9]=2)[CH:4]=[CH:3]1.Cl[C:18](=[O:23])[C:19]([O:21][CH3:22])=[O:20]>C(Cl)Cl>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N:11]3[CH2:12][CH2:13][O:14][CH2:15][CH2:16]3)[CH:9]=2)[C:4]([C:18](=[O:23])[C:19]([O:21][CH3:22])=[O:20])=[CH:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

1-Methyl-6-morpholin-4-yl-1H-indole (3.89 g, 18 mmol) was dissolved in CH2Cl2 (18 mL) and cooled at 0° C. Methyl chlorooxoacetate (2.4 mL, 26 mmol) was added to give a dark solution. Stirring was continued for 2 h at 0° C. and more methyl chlorooxoacetate (0.40 mL, 4.3 mmol) was added. After a further 2 h, the solvent was evaporated. The resulting solid was taken up in ether, filtered and washed well with ether to give crude methyl (1-methyl-6-morpholin-4-yl-1H-indol-3-yl)glyoxylate (6 g).

Workup

customto give a dark solution
waitAfter a further 2 h
customthe solvent was evaporated
filtrationfiltered
washwashed well with ether

Sources & evidence

ORD record: ord-0a0cc69973674b51a6d140f6456c249d
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06281356B1

Reaction notes

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