Lawesson's reagent → Ethyl 5-{7-(benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl}-1,3,4-thiadiazole-2-carboxylate

HRID 1188985Notes

Reaction equation

HRID 1188985 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([O:29][C:30]2[CH:35]=[CH:34][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:32][CH:31]=2)[CH:12]=[C:13]2[C:17]=1[NH:16][C:15]([C:18]([NH:20][NH:21][C:22](=O)[C:23]([O:25][CH2:26][CH3:27])=[O:24])=O)=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:49])=CC=1>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([O:29][C:30]2[CH:35]=[CH:34][C:33]([S:36]([CH3:39])(=[O:37])=[O:38])=[CH:32][CH:31]=2)[CH:12]=[C:13]2[C:17]=1[NH:16][C:15]([C:18]1[S:49][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N:21][N:20]=1)=[CH:14]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagent2×HCID 66897270Ethyl [2-({7-(benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl}carbonyl)hydrazino](oxo)acetate

Product 1

HCID 136337862Ethyl 5-{7-(benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl}-1,3,4-thiadiazole-2-carboxylateYield 74.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl [2-({7-(benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl}carbonyl)hydrazino](oxo)acetate (420 mg) was dissolved in tetrahydrofuran (15 mL), Lawesson's reagent (308 mg) was added, and the mixture was stirred at 50° C. for 5 hr. Lawesson's reagent (300 mg) was added again to the reaction solution, and the mixture was further stirred at 50° C. for 1 hr. The reaction solution was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=10:90-40:60, volume ratio), and the obtained yellow oil was crystallized from methanol to give the title compound (310 mg, yield 74%) as pale-yellow crystals. The obtained crystals was recrystallized from ethyl acetate-diethyl ether to give pale-yellow crystals. melting point 194-195° C. MS 550 (MH+).

Workup

  1. stirringthe mixture was further stirred at 50° C. for 1 hr
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customthe obtained yellow oil was crystallized from methanol

Sources & evidence

ORD record
ord-66b2ec7d18024c36907953986082abdf
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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