Triethylamine → HCID 57458159, compound

HRID 1693063Notes

Reaction equation

HRID 1693063 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(diphenylphophino)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 (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, then 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
  4. dry with materialbrine, dried 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-0e02d6c3793c496b90a381135fd19ef6
Source dataset
uspto-grants-2012_04
Patent number
US08158650B2

Reaction notes

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