Tributylphosphine → HCID 58237092, compound

HRID 1189016Notes

Reaction equation

HRID 1189016 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[C:7]([O:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][N:19]=2)[CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([C:14]([NH2:16])=O)=[CH:10]2)[CH3:3].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:37])=CC=1.[C:50]([O:55][CH2:56][CH3:57])(=[O:54])[C:51]#[C:52][CH3:53].C(P(CCCC)CCCC)CCC>O1CCCC1>[CH3:3][CH:2]([O:4][C:5]1[CH:6]=[C:7]([O:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][N:19]=2)[CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([C:14]1[S:37][CH:52]([CH2:51][C:50]([O:55][CH2:56][CH3:57])=[O:54])[CH2:53][N:16]=1)=[CH:10]2)[CH3:1]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 78043Ethyl 2-butynoateHCID 87949Lawesson's reagentHCID 58237121HCID 58237121, compound

Product 1

HCID 58237092HCID 58237092, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

A mixture of 7-(1-methylethoxy)-5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-1H-indole-2-carboxamide (2.0 g), Lawesson's reagent (2.27 g) and tetrahydrofuran (70 mL) was stirred at 65° C. for 1 h. The mixture was concentrated in vacuo. Toluene and diisopropyl ether were added to the residue to give crystals. The crystals were collected by filtration and washed with toluene-diisopropyl ether to give yellow crystals. A mixture of the crystals, ethyl 2-butynoate (1.44 g), tributylphosphine (1.03 g) and tetrahydrofuran (100 mL) was stirred at 70° C. for 2 h, and then concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate:hexane=1:4 to 2:1, volume ratio) to give the title compound (1.18 g, 45%) as a yellow amorphous solid. MS 518 (MH+).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionToluene and diisopropyl ether were added to the residue
  3. customto give crystals
  4. filtrationThe crystals were collected by filtration
  5. washwashed with toluene-diisopropyl ether
  6. customto give yellow crystals
  7. stirringwas stirred at 70° C. for 2 h
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel chromatography (ethyl acetate:hexane=1:4 to 2:1, volume ratio)

Sources & evidence

ORD record
ord-c20ecc8be3ea4fb9aee9dc414dc4ed92
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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