Sodium Bromide → HCID 67355236, compound

HRID 2272286Notes

Reaction equation

HRID 2272286 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[C:18](OS(C(F)(F)F)(=O)=O)=[CH:17][C:11]=3[C:12]=2[C:13]([O:15][CH3:16])=[O:14])=[CH:4][CH:3]=1.[CH:32]1(B(O)O)[CH2:34][CH2:33]1.[F-].[K+].[Br-].[Na+]>C1(C)C=CC=CC=1.O.C(OCC)(=O)C.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>[CH:32]1([C:18]2[C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:10]3[O:9][C:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)=[C:12]([C:13]([O:15][CH3:16])=[O:14])[C:11]=3[CH:17]=2)[CH2:34][CH2:33]1

Participants

9

Reactant 4

HCID 253881Sodium BromideHCID 522689Potassium FluorideHCID 2760897Cyclopropylboronic acidHCID 86696007HCID 86696007, compound

Product 1

HCID 67355236HCID 67355236, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 2-(4-fluorophenyl)-6-nitro-5-{[(trifluoromethyl)sulfonyl]oxy}-1-benzofuran-3-carboxylate (7.12 g, 15.37 mmol), cyclopropylboronic acid (2.19 g, 25.5 mmol), potassium fluoride (3.26 g, 56.1 mmol), sodium bromide (1.75 g, 17.01 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.85 g, 0.736 mmol) were stirred together under nitrogen in a mixture of toluene (90 mL) and water (2.25 mL) and heated at 100° C. for 18 hours. The reaction mixture was cooled, diluted with ethyl acetate and washed with water. The organic phase was separated, dried by hydrophobic filter tube and evaporated under vacuum. The residue was purified by flash chromatography, eluting over silica gel with a gradient of 0-5% ethyl acetate in cyclohexane. Product containing fractions were evaporated under vacuum to give the methyl 5-cyclopropyl-2-(4-fluorophenyl)-6-nitro-1-benzofuran-3-carboxylate. LCMS (m/z, ES+)=728 (2M+NH4)+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with water
  3. customThe organic phase was separated
  4. customdried by hydrophobic filter tube
  5. customevaporated under vacuum
  6. customThe residue was purified by flash chromatography
  7. washeluting over silica gel with a gradient of 0-5% ethyl acetate in cyclohexane
  8. additionProduct containing fractions
  9. customwere evaporated under vacuum

Sources & evidence

ORD record
ord-c684d7ca029248e9b84f079a5f82cc18
Source dataset
uspto-grants-2015_09
Patent number
US09119868B2

Reaction notes

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