3-Trifluoroacetyl-5-methoxy-2-methylindole → Ethyl 3-(5-methoxy-2-methylindol-3-yl)-4,4,4-trifluoro-2-butenoate

HRID 1451525Notes

Reaction equation

[F:1][C:2]([F:18])([F:17])[C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[NH:7][C:6]=1[CH3:16])=O.[C:19]([C:24]1C=CC=CC=1P(=C)(C1C=CC=CC=1)C1C=CC=CC=1)([O:21][CH2:22][CH3:23])=[O:20]>C1(C)C=CC=CC=1>[CH3:15][O:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:16])=[C:5]2[C:3]([C:2]([F:18])([F:17])[F:1])=[CH:24][C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

Conditions

Temperature: 120 °C

Procedure

A suspension of the indole from Step 1 (18.3 g, 71.4 mmol) and carbethoxy-methylenetriphenylphosphorane (49.7 g, 142.8 mmol) in 100 mL of toluene was pressurized to 900 psi nitrogen in a stainless steel, high pressure Parr reactor and was heated to 120° C. for 39 h. The reaction mixture was cooled, concentrated and purified by flash chromatography (30% ethyl acetate/hexanes) to give 23 g of the title compound as a mixture of E- and Z- isomers.

Workup

temperatureThe reaction mixture was cooled
concentrationconcentrated
custompurified by flash chromatography (30% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-7c3102d6c9424535a14510073a12373a
Source dataset: uspto-grants-1997_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05604253

Reaction notes

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