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Water → 2-{2-[5-{[5-(Methylsulfonyl)pyridin-2-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}ethanol

HRID 1042155
Notes
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Reaction equation

HRID 1042155 reaction equation
C([O:3][C:4](=O)[CH2:5][CH:6]1[S:10][C:9]([C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([O:20][C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][N:22]=2)=[CH:15][C:14]=3[O:31][CH:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[N:8][CH2:7]1)C.[BH4-].[Li+].O.C(OCC)(=O)C>O1CCCC1.CO.CCCCCC>[CH3:30][S:27]([C:24]1[CH:25]=[CH:26][C:21]([O:20][C:16]2[CH:17]=[C:18]3[C:13](=[C:14]([O:31][CH:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)[CH:15]=2)[NH:12][C:11]([C:9]2[S:10][CH:6]([CH2:5][CH2:4][OH:3])[CH2:7][N:8]=2)=[CH:19]3)=[N:22][CH:23]=1)(=[O:28])=[O:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4148881Lithium borohydride3×HCID 68090828Ethyl{2-[5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetate

Product 1

HCID 667262092-{2-[5-{[5-(Methylsulfonyl)pyridin-2-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}ethanol
Yield 52%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent3×HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Ethyl{2-[5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetate (207 mg) was dissolved in tetrahydrofuran (5 mL)-methanol (2 mL), lithium tetrahydroborate (22 mg) was added under ice-cooling, and the mixture was stirred at room temperature for 50 min. To the reaction solution were added lithium tetrahydroborate (32 mg) and methanol (1 mL), and the mixture was stirred at room temperature for 1 hr. Furthermore, lithium tetrahydroborate (15 mg) was added, and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (methanol:ethyl acetate:hexane=0:50:50 to 20:80:0, volume ratio) to give the title compound as a yellow amorphous solid (99 mg, yield 52%). The obtained amorphous solid was crystallized from diethyl ether, and the obtained crystals were recrystallized from ethyl acetate-diethyl ether to give the title compound as colorless crystals.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. stirringthe mixture was stirred at room temperature for 1 hr
  4. stirringthe mixture was stirred at room temperature for 1 hr
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe obtained crude product

Sources & evidence

ORD record
ord-2fb44e6d1bec4822ad9e1cd89486af94
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08557805B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes