Acetic Acid → HCID 53704947, compound

HRID 1609397Notes

Reaction equation

C1(N=C=NC2CCCCC2)CCCCC1.[CH3:16][N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([C:26](=[O:30])[C:27]([OH:29])=[O:28])=[CH:18]1.[F:31][C:32]1[C:37](O)=[C:36]([F:39])[C:35]([F:40])=[C:34]([F:41])[C:33]=1[F:42].C(O)(=O)C>O1CCCC1>[CH3:16][N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([C:26](=[O:30])[C:27]([O:29][C:37]2[C:36]([F:39])=[C:35]([F:40])[C:34]([F:41])=[C:33]([F:42])[C:32]=2[F:31])=[O:28])=[CH:18]1

Participants

Conditions

Temperature: 0 °C

Procedure

1.13 g (5.5 mol) of dicyclohexylcarbodiimide were added to a solution, cooled in ice, of 1 g (5 mmol) of 1-methylindole-3glyoxylic acid and 1.01 g (5 mmol) of pentafluorophenol in 50 ml of dry tetrahydrofuran. After stirring for 4 hours under a nitrogen atmosphere at 0° C., the mixture was allowed to warm to room temperature and left to stand for 60 hours. Then, 3 ml of glacial acetic acid were added and the mixture obtained was filtered. The filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel using dichloromethane for the elution to give 404 mg (22%) of pentafluorophenyl 1-methylindole-3-glyoxylate in the form of a pale yellow solid of melting point 168°-9° C.

Workup

temperatureto warm to room temperature
waitleft
waitto stand for 60 hours
customthe mixture obtained
filtrationwas filtered
concentrationThe filtrate was concentrated under reduced pressure
customThe residue was purified by flash chromatography on silica gel
washfor the elution

Sources & evidence

ORD record: ord-6811b0b444764a80a8ee0a479cd84ba1
Source dataset: uspto-grants-1995_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05399712

Reaction notes

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