Triphenylarsine → HCID 69659014, compound

HRID 2212966Notes

Reaction equation

HRID 2212966 reaction equation
[C:1]1([CH3:34])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]#[N:20])=[CH:16][CH:17]=3)[C:12]([Sn](CCCC)(CCCC)CCCC)=[CH:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:35]([O:37][C:38]([C:40]1[CH2:44][CH2:43][CH2:42][C:41]=1OS(C(F)(F)F)(=O)=O)=[O:39])[CH3:36].C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C>[CH2:35]([O:37][C:38]([C:40]1[CH2:44][CH2:43][CH2:42][C:41]=1[C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[C:15]([C:19]#[N:20])[CH:14]=2)[N:10]([S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:34])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH:11]=1)=[O:39])[CH3:36]

Participants

5

Reactant 3

HCID 11773TriphenylarsineHCID 2779887Ethyl 2-[(trifluoromethanesulfonyl)oxy]cyclopent-1-ene-1-carboxylateHCID 21955928HCID 21955928, compound

Product 1

HCID 69659014HCID 69659014, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

1-(Toluene-4-sulfonyl)-3-tributylstannanyl-1H-indole-5-carbonitrile (5.60 g, 9.56 mMol), 2-trifluoromethanesulfonyloxy-cyclopent-1-enecarboxylic acid ethyl ester (2.75 g, 9.56 mMol), triphenyl arsine (0.29 g, 0.96 mMol) and tris(dibenzylidenacetone)dipalladium(0) (0.44 g, 0.48 mMol) were dissolved in DMF and degassed for 5 min with a stream of nitrogen. The reaction was heated under nitrogen at 60° C. for 5 min. The reaction was poured into brine (500 mL) and extracted with ethyl acetate (2×100 mL). The organics were mixed with saturated aqueous potassium fluoride (100 mL) and the resulting solids were removed by filtration through celite. The layers of the filtrate were separated and the organic layer was dried with magnesium sulfate and evaporated in vacuo. The solid product was recrystallized from hot ethyl acetate/hexanes to provide the product as a white solid (3.04 g, 73%). 1H NMR (400 MHz, CDCl3) δ 8.05 (1H, d, J=8.7 Hz), 7.87 (1H, s), 7.79 (2H, d, J=8.5 Hz), 7.71 (1H, d, J=1.2 Hz), 7.53 (1H, dd, J=8.8, 1.5 Hz), 7.27 (2H, m), 4.01 (2H, q, J=6.9 Hz), 2.86 (4H, m), 2.36 (3H, s), 2.03 (2H, pentet, J=7.7 Hz), 0.95 (3H, t, J=7.1 Hz); MS m/e 457.0 (M+Na).

Workup

  1. customdegassed for 5 min with a stream of nitrogen
  2. additionThe reaction was poured into brine (500 mL)
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. additionThe organics were mixed with saturated aqueous potassium fluoride (100 mL)
  5. customthe resulting solids were removed by filtration through celite
  6. customThe layers of the filtrate were separated
  7. dry with materialthe organic layer was dried with magnesium sulfate
  8. customevaporated in vacuo
  9. customThe solid product was recrystallized from hot ethyl acetate/hexanes

Sources & evidence

ORD record
ord-a0b061b096ae4d28bc4559c6a614c98d
Source dataset
uspto-grants-2006_09
Patent number
US07105516B2

Reaction notes

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