Triethylamine → HCID 57458159, compound

HRID 1924790Notes

Reaction equation

HRID 1924790 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:8]=2)[CH:3]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.C[CH2:53][O:54][C:55](C)=[O:56].C1(C)C=CC=CC=1>CO.CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:12]([C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([C:55]([O:54][CH3:53])=[O:56])[CH:11]=[CH:10]2)([CH3:15])([CH3:14])[CH3:13]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 21584019Toluene ethylacetateHCID 53420556HCID 53420556, compound

Product 1

HCID 57458159HCID 57458159, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-bromo-6-tert-butylnaphthalene (980 mg, 3.72 mmol), palladium acetate (84 mg, 0.37 mmol), 1,3-bis(diphenylphosphino)propane (153 mg, 0.37 mmol) and triethylamine (1.56 ml, 11.2 mmol) in MeOH (6 ml) and DMF (10 ml) was heated at 80° C. under carbon monooxide gas pressure using with balloon for 15 hours. After cooling to ambient temperature, the mixture was diluted with EtOAc-toluene (8:1)(160 ml) and filtered through a pad of celite. The filtrate and washings were washed with water, brine, dried over sodium sulfate and evaporated in vacuo to give the crude product which was purified through silica gel column chromatography eluting with hexane/EtOAc (10:1) to furnish the title compound as colorless oil (843 mg, 94%). 1H NMR (CDCl3): δ 1.43 (9H, s), 3.97 (3H, s), 7.61-7.67 (1H, m), 7.79-7.93 (3H, m), 8.01-8.07 (1H, m), 8.57 (1H, br, s).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. filtrationfiltered through a pad of celite
  3. washThe filtrate and washings were washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customto give the crude product which
  7. customwas purified through silica gel column chromatography
  8. washeluting with hexane/EtOAc (10:1)

Sources & evidence

ORD record
ord-df592d5ea1b54adaac4e4a0591bd29fe
Source dataset
uspto-grants-2012_05
Patent number
US08178558B2

Reaction notes

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