Tetrahydrofuran → HCID 136060802, compound

HRID 1851505Notes

Reaction equation

HRID 1851505 reaction equation
[C:1]([C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[NH:12][S:13]([C:16]1[S:17][CH:18]=[CH:19][CH:20]=1)(=[O:15])=[O:14])#[N:2].C[Si]([N:25]=[N+:26]=[N-:27])(C)C.C([Sn](=O)CCCC)CCC.O1CCCC1>C(OCC)(=O)C>[N:2]1[NH:25][N:26]=[N:27][C:1]=1[C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[NH:12][S:13]([C:16]1[S:17][CH:18]=[CH:19][CH:20]=1)(=[O:14])=[O:15]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 57901755HCID 57901755, compound

Product 1

HCID 136060802HCID 136060802, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-(2-cyano-1H-indol-7-yl)thiophene-2-sulfonamide (0.40 g), trimethylsilylazide (0.35 mL), dibutyltin oxide (33 mg) and tetrahydrofuran (15 mL) was heated under reflux overnight. To the reaction mixture was added ethyl acetate, the mixture was ice-cooled, and the resulting crystals were filtrated, washed with cold ethyl acetate, and dried to give the title compound (0.09 g, yield 23%) as pale-yellow crystals. The crystals were recrystallized from ethyl acetate-hexane. melting point 274-275° C. (decomposition).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. temperaturecooled
  4. filtrationthe resulting crystals were filtrated
  5. washwashed with cold ethyl acetate
  6. customdried

Sources & evidence

ORD record
ord-d3c9932f76f8462481dc68b8a00aa6a3
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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