Triethylamine → HCID 57458159, compound

HRID 2425562Notes

Reaction equation

HRID 2425562 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:52]([O:55][CH2:56]C)(=[O:54])C.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:52]([O:55][CH3:56])=[O:54])[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 methanol (6 ml) and DMF (10 ml) was heated at 80° C. under carbon monoxide gas pressure (balloon) for 15 hours. After cooling to ambient temperature, the mixture was diluted with ethyl acetate-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 (300 MHz, 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-ee0e258f3c404104b8c016b13e7d92b9
Source dataset
uspto-grants-2011_06
Patent number
US07964732B2

Reaction notes

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