1,2-Dimethoxyethane → HCID 67959218, compound

HRID 1404997Notes

Reaction equation

HRID 1404997 reaction equation
CC1(C)C(C)(C)OB([C:9]2[C:18]3[O:17][CH2:16][CH2:15][N:14]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:13][C:12]=3[S:11][CH:10]=2)O1.Br[C:28]([C:30]([F:33])([F:32])[F:31])=[CH2:29].C(=O)([O-])[O-].[Na+].[Na+].C(COC)OC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[F:31][C:30]([F:33])([F:32])[C:28]([C:9]1[C:18]2[O:17][CH2:16][CH2:15][N:14]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:13][C:12]=2[S:11][CH:10]=1)=[CH2:29]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2726961-Propene, 2-bromo-3,3,3-trifluoro-HCID 67959390HCID 67959390, compound

Product 1

HCID 67959218HCID 67959218, compoundYield 50.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of tert-butyl 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydrothieno[2,3-f][1,4]oxazepine-4(5H)-carboxylate (300 mg), 2-bromo-3,3,3-trifluoropropene (0.2 ml), tetrakis(triphenylphosphine)palladium(0) (25.5 mg), saturated aqueous sodium carbonate solution (7 ml) and dimethoxyethane (10 ml) was stirred at 85° C. for 12 hr under an argon atmosphere. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give the title compound (140 mg, 50.9%) as an oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-30ecd6fecb80462a8b0427dde3498d23
Source dataset
uspto-grants-2014_12
Patent number
US08916549B2

Reaction notes

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