2-[1-[4-(2-ethoxy-ethanesulfonyl)-phenyl]-2-(tetrahydro-pyran-4-yl)-vinyl]-5-fluoro-1H-pyrrolo[2,3-b]pyridine → 2-[1-[4-(2-ethoxy-ethanesulfonyl)-phenyl]-2-(tetrahydro-pyran-4-yl)-ethyl]-5-fluoro-1H-pyrrolo[2,3-b]pyridine

HRID 1515812Notes

Reaction equation

HRID 1515812 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:23]2[NH:32][C:26]3=[N:27][CH:28]=[C:29]([F:31])[CH:30]=[C:25]3[CH:24]=2)=[CH:16][CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:11][CH:10]=1)(=[O:8])=[O:7])[CH3:2]>[Pd].CO>[CH2:1]([O:3][CH2:4][CH2:5][S:6]([C:9]1[CH:10]=[CH:11][C:12]([CH:15]([C:23]2[NH:32][C:26]3=[N:27][CH:28]=[C:29]([F:31])[CH:30]=[C:25]3[CH:24]=2)[CH2:16][CH:17]2[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)=[CH:13][CH:14]=1)(=[O:7])=[O:8])[CH3:2]

Participants

4

Reactant 1

HCID 672277942-[1-[4-(2-ethoxy-ethanesulfonyl)-phenyl]-2-(tetrahydro-pyran-4-yl)-vinyl]-5-fluoro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 672292622-[1-[4-(2-ethoxy-ethanesulfonyl)-phenyl]-2-(tetrahydro-pyran-4-yl)-ethyl]-5-fluoro-1H-pyrrolo[2,3-b]pyridineYield 58.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-[1-[4-(2-ethoxy-ethanesulfonyl)-phenyl]-2-(tetrahydro-pyran-4-yl)-vinyl]-5-fluoro-1H-pyrrolo[2,3-b]pyridine (250 mg, 0.54 mmol) and 10% palladium on activated carbon (74 mg) in methanol (250 mL) was heated at 50° C. under hydrogen (50 psi) for 5 h. The mixture was cooled to 25° C., the solids filtered off, washed with ethyl acetate and concentrated in vacuo. Purification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 50% dichloromethane/ethyl acetate) afforded 2-[1-[4-(2-ethoxy-ethanesulfonyl)-phenyl]-2-(tetrahydro-pyran-4-yl)-ethyl]-5-fluoro-1H-pyrrolo[2,3-b]pyridine (145 mg, 57%): LC/MS m/e calcd for C24H29FN2O4S [M+H]+ 461.57, observed 461.1.

Workup

  1. temperatureThe mixture was cooled to 25° C.
  2. filtrationthe solids filtered off
  3. washwashed with ethyl acetate
  4. concentrationconcentrated in vacuo
  5. customPurification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 50% dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-afba97468a924bb0b69e9799ca8361d2
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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