Tetrahydrofuran → HCID 66898283, compound

HRID 1189005Notes

Reaction equation

HRID 1189005 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([CH2:29][O:30][CH3:31])[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][N:20]=2)[CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15](=[S:17])[NH2:16])=[CH:11]2.[C:32]([O:37][CH2:38][CH3:39])(=[O:36])[C:33]#[C:34][CH3:35].C(P(CCCC)CCCC)CCC.O1CCCC1>C1(C)C=CC=CC=1>[CH3:1][O:2][CH2:3][CH:4]([CH2:29][O:30][CH3:31])[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:26])=[O:27])=[CH:21][N:20]=2)[CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15]1[S:17][CH:34]([CH2:33][C:32]([O:37][CH2:38][CH3:39])=[O:36])[CH2:35][N:16]=1)=[CH:11]2

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 13831TributylphosphineHCID 78043Ethyl 2-butynoateHCID 86652848HCID 86652848, compound

Product 1

HCID 66898283HCID 66898283, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 7-[2-methoxy-1-(methoxymethyl)ethoxy]-5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-1H-indole-2-carbothioamide (1.69 g), ethyl 2-butynoate (0.84 mL), tributylphosphine (0.9 mL), tetrahydrofuran (20 mL) and toluene (30 mL) was stirred at 50° C. for 13 h. The mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (methanol/ethyl acetate/hexane=0/20/80 to 5/95/0, volume ratio), followed by basic silica gel column chromatography (ethyl acetate/hexane=20/80 to 90/10, volume ratio) to give the title compound (1.14 g, 55%) as a brownish amorphous solid. MS 578 (MH+).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (methanol/ethyl acetate/hexane=0/20/80 to 5/95/0, volume ratio)

Sources & evidence

ORD record
ord-05ccbfbeed074b529a1c4e5fec81f998
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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