Stannane, tributyl(1-ethoxyethenyl)- → HCID 66791179, compound

HRID 1672296Notes

Reaction equation

HRID 1672296 reaction equation
[NH2:1][C:2]1[CH:21]=[C:20](Br)[C:5]2[N:6]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[O:9][C:4]=2[CH:3]=1.C([Sn](CCCC)(CCCC)[C:28]([O:30][CH2:31][CH3:32])=[CH2:29])CCC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1>[NH2:1][C:2]1[CH:21]=[C:20]([C:28]([O:30][CH2:31][CH3:32])=[CH2:29])[C:5]2[N:6]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[O:9][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 66789962HCID 66789962, compound

Product 1

HCID 66791179HCID 66791179, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 7-amino-5-bromo-4-(4-fluorophenyl)-2,2-dimethyl-2H-1,4-benzoxazin-3(4H)-one (compound obtained in Reference Example 53(7); 100 mg), tributyl(1-ethoxyvinyl)tin (278 μL), dichlorobis(triphenylphosphine)palladium(II) (19 mg) and toluene was heated at 100° C. under argon atmosphere for 4 hours. After cooling, the reaction mixture was filtered through a NH-silica gel pad, and the filtrate was concentrated in vacuo to give 7-amino-5-(1-ethoxyvinyl)-4-(4-fluorophenyl)-2,2-dimethyl-2H-1,4-benzoxazin-3(4H)-one as a crude product.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered through a NH-silica gel pad
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-38f9a6e2878b42408891f7ecbb5dbbfc
Source dataset
uspto-grants-2011_08
Patent number
US07998956B2

Reaction notes

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