Tetrahydrofuran → HCID 70963859, compound

HRID 1189007Notes

Reaction equation

HRID 1189007 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:15][C:16]2[CH:17]=[N:18][C:19]([CH2:22][O:23][CH3:24])=[CH:20][CH:21]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12](=[S:14])[NH2:13])=[CH:8]2.[C:25]([O:30][CH2:31][CH3:32])(=[O:29])[C:26]#[C:27][CH3:28].C(P(CCCC)CCCC)CCC.O1CCCC1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:15][C:16]2[CH:17]=[N:18][C:19]([CH2:22][O:23][CH3:24])=[CH:20][CH:21]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:14][CH:27]([CH2:26][C:25]([O:30][CH2:31][CH3:32])=[O:29])[CH2:28][N:13]=1)=[CH:8]2

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 13831TributylphosphineHCID 78043Ethyl 2-butynoateHCID 86652849HCID 86652849, compound

Product 1

HCID 70963859HCID 70963859, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 7-methoxy-5-{[6-(methoxymethyl)pyridin-3-yl]oxy}-1H-indole-2-carbothioamide (2.04 g), ethyl 2-butynoate (1.8 mL), tributylphosphine (1.5 mL), tetrahydrofuran (25 mL) and toluene (30 mL) was stirred at 50° C. for 1 h. The mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90 to 70/30, volume ratio) to give the title compound (1.36 g, 52%) as a yellow amorphous solid. MS 578 (MH+).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90 to 70/30, volume ratio)

Sources & evidence

ORD record
ord-dc784ef627bc4761b451aeb113c64a46
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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