2-(Benzyloxy) ethanol → ethyl 5-fluoro-1-(2-benzyloxyethyl)-1H-indole-2-carboxylate

HRID 1097258Notes

Reaction equation

[CH2:1]([O:8][CH2:9][CH2:10]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C=P(C)(C)C)#N.[F:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:23]2>C1(C)C=CC=CC=1>[F:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[N:25]([CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:24]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:23]2

Participants

Conditions

Temperature: 20 °C

Procedure

94 μl (0.657 mmol) of 2-benzyloxyethanol and 50.4 mg (0.438 mmol) of (cyanomethylene)trimethylphosphorane (Tet. Lett., 1996, 37, 2459-2462) are added to a solution of 68 mg (0.329 mmol) of ethyl 5-fluoro-1H-indole-2-carboxylate in 2 ml of toluene, stirred at 20° C. The reaction mixture is heated at 110° C. for 12 hours and then concentrated under reduced pressure, taken up in 20 ml of ethyl ether, filtered over a celite buffer and concentrated under reduced pressure. The residue obtained is purified by preparative HPLC, elution being carried out with a mixture of water, acetonitrile and trifluoroacetic acid. 99 mg of a yellow oil are thus isolated.

Workup

temperatureThe reaction mixture is heated at 110° C. for 12 hours
concentrationconcentrated under reduced pressure
filtrationfiltered over a celite buffer and
concentrationconcentrated under reduced pressure
customThe residue obtained
customis purified by preparative HPLC, elution
additionbeing carried out with a mixture of water, acetonitrile and trifluoroacetic acid

Sources & evidence

ORD record: ord-0f405a7e438d4facac24934ed65fcd91
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143248B2

Reaction notes

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