Tributylphosphine → HCID 58236999, compound

HRID 1189012Notes

Reaction equation

HRID 1189012 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([CH3:29])[O:5][C:6]1[CH:7]=[C:8]([O:18][C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)[CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15]([NH2:17])=O)=[CH:11]2.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:39])=CC=1.[C:52]([O:57][CH2:58][CH3:59])(=[O:56])[C:53]#[C:54][CH3:55].C(P(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][O:2][CH2:3][CH:4]([CH3:29])[O:5][C:6]1[CH:7]=[C:8]([O:18][C:19]2[CH:20]=[CH:21][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:23][CH:24]=2)[CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15]1[S:39][CH:54]([CH2:53][C:52]([O:57][CH2:58][CH3:59])=[O:56])[CH2:55][N:17]=1)=[CH:11]2

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 78043Ethyl 2-butynoateHCID 87949Lawesson's reagentHCID 58237016HCID 58237016, compound

Product 1

HCID 58236999HCID 58236999, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of 7-(2-methoxy-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxamide (874 mg) in tetrahydrofuran (20 mL) was added Lawesson's reagent (845 mg) at room temperature. The mixture was stirred at 50° C. for 45 min, and then cooled to room temperature. The mixture was concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate:hexane=50:50 to 100:0, volume ratio) to give a yellow amorphous solid. To a solution of the solid in tetrahydrofuran (20 mL) were added ethyl 2-butynoate (0.507 mL) and tributylphosphine (0.652 mL). The whole was stirred at 50° C. for 45 min. The mixture was cooled to room temperature and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate:hexane=50:50 to 100:0) to give the title compound (531 mg, 46%) as a brown amorphous solid. MS 547 (MH+).

Workup

  1. temperaturecooled to room temperature
  2. concentrationThe mixture was concentrated in vacuo
  3. customThe residue was purified by silica gel chromatography (ethyl acetate:hexane=50:50 to 100:0, volume ratio)
  4. customto give a yellow amorphous solid
  5. stirringThe whole was stirred at 50° C. for 45 min
  6. temperatureThe mixture was cooled to room temperature
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography (ethyl acetate:hexane=50:50 to 100:0)

Sources & evidence

ORD record
ord-f34958a8ea254649b8fa2aa00b56af39
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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