Sodium hydride → HCID 54147595, compound

HRID 1638461Notes

Reaction equation

HRID 1638461 reaction equation
[CH3:1][N:2]([CH:4]=[C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]1=[O:14])[CH3:3].Br[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([F:24])[CH:17]=1.[H-].[Na+]>CCOCC.CCCCC>[F:24][C:18]1[CH:17]=[C:16]([N:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:5](=[CH:4][N:2]([CH3:1])[CH3:3])[C:6]2=[O:14])[CH:21]=[CH:20][C:19]=1[O:22][CH3:23]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 753784-Bromo-2-fluoroanisoleHCID 30289742H-Indol-2-one, 3-[(dimethylamino)methylene]-1,3-dihydro-, (Z)-

Product 1

HCID 54147595HCID 54147595, compound

Reagents, catalysts & solvents 1

HCID 21877078Diethylether pentaneSolvent

Procedure

By the procedure of Example C1, without chromatography, but directly crystallizing the crude product from ether/pentane, 3-(dimethylaminomethylene)-2-(1H,3H)-indolone (3.77 g, 20 mmoles) and 4-bromo-2-fluoroanisole (4.10 g, 20 mmoles) with NaH (0.96 g of 50% dispersion in oil, 20 mmoles) and Cu2Br2 (5.74 g, 20 mmoles), were converted to title product, 0.79 g, m.p. 113°-114°.

Sources & evidence

ORD record
ord-4446be87b13f498a99cc82ee0290bd0d
Source dataset
uspto-grants-1989_11
Patent number
US04879391

Reaction notes

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