Ethanol → 6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-ol

HRID 1882028Notes

Reaction equation

HRID 1882028 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[NH:16][C:17]([CH:20]([C:28]3[CH:33]=[CH:32][C:31]([S:34]([CH:37]4[CH2:39][CH2:38]4)(=[O:36])=[O:35])=[CH:30][CH:29]=3)[CH2:21][CH:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:18][CH:19]=2)=[N:13][CH:14]=1)C1C=CC=CC=1.C(O)C>[C].[Pd].O1CCCC1>[CH:37]1([S:34]([C:31]2[CH:32]=[CH:33][C:28]([CH:20]([C:17]3[NH:16][C:15]([C:12]4[N:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=4)=[CH:19][CH:18]=3)[CH2:21][CH:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:29][CH:30]=2)(=[O:36])=[O:35])[CH2:39][CH2:38]1

Participants

5

Reactant 2

HCID 702EthanolHCID 593314045-(benzyloxy)-2-(5-[1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl]-1H-pyrrol-2-yl)pyridine

Product 1

HCID 593314946-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-olYield 99%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(benzyloxy)-2-(5-[1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl]-1H-pyrrol-2-yl)pyridine (1.97 g) in a mixed solvent of ethanol (30 mL) and tetrahydrofuran (30 mL) was added 10% palladium carbon (200 mg), and the mixture was stirred at room temperature for 16 hr under a hydrogen atmosphere. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=20:80-80:20, volume ratio) to give the title compound (1.62 g, yield 99%) as a yellow amorphous solid. MS: 453 (MH+).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=20:80-80:20, volume ratio)

Sources & evidence

ORD record
ord-02e09e45f2af47e39b4c8f6b4b71b6cc
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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