Diethyl Ether → 1-benzyl-5-fluoro-3H-indol-2-one

HRID 1410330Notes

Reaction equation

HRID 1410330 reaction equation
C(N1C2C(=CC=CC=2)CC1=O)C1C=CC=CC=1.[F:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[N:24]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23](=[O:35])[C:22]2=O.CCOCC>CCCCCC>[CH2:28]([N:24]1[C:25]2[C:21](=[CH:20][C:19]([F:18])=[CH:27][CH:26]=2)[CH2:22][C:23]1=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 110971561-Benzyl-5-fluoroindoline-2,3-dioneHCID 117908211-benzyl-1,3-dihydro-2H-indol-2-one

Product 1

HCID 149184901-benzyl-5-fluoro-3H-indol-2-oneYield 75.2%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

The title compound was prepared in a manner similar to the method of N-Benzyl-oxindole using 5-fluoro-N-benzylisatin (14.5 g, 56.8 mmol). Trituration using Et2O:hexane yielded the title compound as a pale yellow solid (10.3 g, 75%). 1H NMR (400 MHz, CDCl3) δ 7.30-7.26 (m, 5H), 7.00 (d, J=7.6 Hz, 1H), 6.87 (t, 1H), 6.63 (m, 1H), 4.91 (s, 2H), 3.63 (s, 2H); MS ESI 241.9 [M+H]+, calcd for [C15H10FNO2+H]+ 241.09.

Sources & evidence

ORD record
ord-f4f2665186594c70ab4612fd0a143f34
Source dataset
uspto-grants-2014_12
Patent number
US08921545B2

Reaction notes

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