Hydrochloric Acid → (5-{7-(Benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl}-1,3,4-thiadiazol-2-yl)methanol

HRID 1188986Notes

Reaction equation

HRID 1188986 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([O:28][C:29]2[CH:34]=[CH:33][C:32]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:31][CH:30]=2)[CH:12]=[C:13]2[C:17]=1[NH:16][C:15]([C:18]1[S:22][C:21]([C:23](OCC)=[O:24])=[N:20][N:19]=1)=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O.Cl>O1CCCC1.CO.CCCCCC.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([O:28][C:29]2[CH:30]=[CH:31][C:32]([S:35]([CH3:38])(=[O:36])=[O:37])=[CH:33][CH:34]=2)[CH:12]=[C:13]2[C:17]=1[NH:16][C:15]([C:18]1[S:22][C:21]([CH2:23][OH:24])=[N:20][N:19]=1)=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 136337862Ethyl 5-{7-(benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl}-1,3,4-thiadiazole-2-carboxylate

Product 1

HCID 136352667(5-{7-(Benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl}-1,3,4-thiadiazol-2-yl)methanolYield 103.6%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 5-{7-(benzyloxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl}-1,3,4-thiadiazole-2-carboxylate (230 mg) was dissolved in a mixed solvent of tetrahydrofuran (8 mL)-methanol (2 mL), sodium borohydride (32 mg) was added under ice-cooling, and the mixture was stirred for 40 min. Water and 1M hydrochloric acid were added to the reaction mixture, and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, filtrated, and concentrated under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (ethyl acetate:hexane=10:90 to 90:10, volume ratio) to give the title compound (220 mg, yield 100%) as a pale-yellow solid. The obtained pale-yellow solid was recrystallized from ethyl acetate-diethyl ether to give pale-yellow crystals. melting point 159-160° C. MS 508 (MH+).

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. extractionthe mixture was subjected to extraction with ethyl acetate
  4. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltrated
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained crude product

Sources & evidence

ORD record
ord-c2317728eaa342c29939eb4e4b0c6249
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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