Diethyl Ether → HCID 53629103, compound

HRID 1851598Notes

Reaction equation

HRID 1851598 reaction equation
[CH2:1]([N:3]([C:12]1[CH:13]=[CH:14][C:15]([CH3:28])=[C:16]2[C:20]=1[NH:19][C:18]([C:21]1[S:22][C:23]([CH:26]=[O:27])=[CH:24][N:25]=1)=[CH:17]2)[S:4]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)(=[O:6])=[O:5])[CH3:2].O1CCC[CH2:30]1.CCOCC.C[Mg]Br>C(OCC)(=O)C>[CH2:1]([N:3]([C:12]1[CH:13]=[CH:14][C:15]([CH3:28])=[C:16]2[C:20]=1[NH:19][C:18]([C:21]1[S:22][C:23]([CH:26]([OH:27])[CH3:30])=[CH:24][N:25]=1)=[CH:17]2)[S:4]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:6])[CH3:2]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 59135759HCID 59135759, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 53629103HCID 53629103, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixed solution of N-ethyl-N-[2-(5-formyl-1,3-thiazol-2-yl)-4-methyl-1H-indol-7-yl]thiophene-2-sulfonamide (0.30 g) and tetrahydrofuran (30 mL) was added ether solution (0.60 mL) of 3M-methylmagnesium bromide under ice-cooling, and the mixture was stirred at the same temperature for 4 hr. The reaction mixture was diluted with ethyl acetate, washed successively with aqueous citric acid solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:2-2:1), and the obtained pale-yellow oil was crystallized from ethyl acetate-hexane to give the title compound (201 mg, yield 65%) as pale-yellow prism crystals. melting point 152-153° C.

Workup

  1. temperaturecooling
  2. washwashed successively with aqueous citric acid solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe obtained pale-yellow oil was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-24485146f44a46ceb6376c99c8f83103
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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