Water → HCID 67455715, compound

HRID 1713264Notes

Reaction equation

HRID 1713264 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH:3]=1.CC1(C)C(C)(C)OB([C:22]2[CH:32]=[CH:31][C:25]([CH2:26][NH:27][C:28](=[O:30])[O-:29])=[CH:24][CH:23]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].O>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C)C=O>[CH2:9]([O:8][C:4]1[CH:3]=[C:2]([C:22]2[CH:23]=[CH:24][C:25]([CH2:26][NH:27][C:28](=[O:30])[O:29][C:25]([CH3:31])([CH3:26])[CH3:24])=[CH:31][CH:32]=2)[CH:7]=[CH:6][CH:5]=1)[CH2:10][CH2:11][CH2:12][CH3:13]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 28102790HCID 28102790, compoundHCID 86613876HCID 86613876, compound

Product 1

HCID 67455715HCID 67455715, compoundYield 113.6%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 1-bromo-3-pentyloxybenzene (0.365 g), tert-bytyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl) benzyl]carbamate (0.575 g), sodium carbonate (0.318 g), water (1.3 mL) and N,N-dimethylformamide (6.5 mL) was added tetrakis(triphenylphosphine) palladium(0) (0.087 g), and the resulting mixture was stirred at 80° C. for 11 hours. The reaction mixture was cooled to room temperature and then partitioned between ethylacetate (35 mL) and water (10 mL). The organic layer was washed successively with water/brine (2/1, 15 mL) and brine (15 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=6/1) to give the title compound (0.437 g)

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between ethylacetate (35 mL) and water (10 mL)
  3. washThe organic layer was washed successively with water/brine (2/1, 15 mL) and brine (15 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on aminopropylated silica gel (eluent: hexane/ethyl acetate=6/1)

Sources & evidence

ORD record
ord-2e554fc7719e437eab89d0373aff120d
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

Loading…