Water → HCID 67455762, compound

HRID 1713318Notes

Reaction equation

HRID 1713318 reaction equation
Br[C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][CH:3]=1.[O:17]1[CH:21]=[CH:20][C:19](B2OC(C)(C)C(C)(C)O2)=[CH:18]1.C(=O)([O-])[O-].[K+].[K+].O>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.CN(C)C=O>[O:17]1[CH:21]=[CH:20][C:19]([C:2]2[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][CH:3]=2)=[CH:18]1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27739962-(Furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 12453839tert-butyl N-[(4-bromophenyl)methyl]carbamate

Product 1

HCID 67455762HCID 67455762, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of tert-butyl N-(4-bromobenzyl)carbamate (0.14 g), 2-(furan-3-yl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane (0.12 g), potassium carbonate (0.1 g), water (0.2 mL) and N,N-dimethylformamide (1 mL) was added tetrakis(triphenylphosphine)palladium(0) (0.03 g), and the resulting mixture was stirred at 80° C. for 12 hours. The reaction mixture was cooled to room temperature and then the insoluble material was filtered out. The filtrate was partitioned between ethyl acetate (110 mL) and water (50 mL). The organic layer was washed successively with water (50 mL) and brine (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on aminopropylated silica gel (eluent: hexane/ethyl acetate=1/1) to give tert-butyl N-[4-(furan-3-yl)benzyl]-carbamate. The compound obtained was dissolved in dichloromethane (5 mL), trifluoroacetic acid (0.57 mL) was added dropwise, and the resulting mixture was stirred at room temperature for 2 hours. Saturated aqueous sodium hydrogen carbonate (15 mL) was added dropwise and the whole was extracted with dichloromethane (30 mL). The organic layer was washed with saturated aqueous sodium hydrogen carbonate/brine (1/1, 10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound (0.06 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe insoluble material was filtered out
  3. customThe filtrate was partitioned between ethyl acetate (110 mL) and water (50 mL)
  4. washThe organic layer was washed successively with water (50 mL) and brine (50 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on aminopropylated silica gel (eluent: hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-34fe5c2edf884178a488204b09e95f76
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

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