Tetrahydrofuran → HCID 57901756, compound

HRID 1851455Notes

Reaction equation

HRID 1851455 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([NH:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19](OCC)=[O:20])=[CH:15]2)(=[O:8])=[O:7].O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>C(O)C>[OH:20][CH2:19][C:16]1[NH:17][C:18]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[NH:9][S:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)(=[O:8])=[O:7]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 4076385HCID 4076385, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 57901756HCID 57901756, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of ethyl 7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxylate (0.76 g) and tetrahydrofuran (15 mL) was added lithium aluminum hydride (0.15 g) at 0° C., and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added ethanol (5 mL), and saturated aqueous ammonium chloride solution (0.5 mL) was added. The resulting inorganic salt was removed by filtration, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography, and the title compound (0.55 g, yield 82%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio). melting point>173° C. (decomposition).

Workup

  1. additionwas added
  2. customThe resulting inorganic salt was removed by filtration
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-34746676f09d48ce9a9797f4b30e755d
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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