Methanol → 2-[2-(2,6-difluoro-3,5-dimethoxyphenyl)ethyl]-5-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazine

HRID 1052311Notes

Reaction equation

HRID 1052311 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([F:12])[C:3]=1[C:13]#[C:14][C:15]1[N:16]=[C:17]2[CH:23]=[CH:22][N:21]([S:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)(=[O:26])=[O:25])[C:18]2=[N:19][CH:20]=1.CO>O1CCCC1.[Pd]>[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([F:12])[C:3]=1[CH2:13][CH2:14][C:15]1[N:16]=[C:17]2[CH:23]=[CH:22][N:21]([S:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)(=[O:26])=[O:25])[C:18]2=[N:19][CH:20]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 899632732-[(2,6-difluoro-3,5-dimethoxyphenyl)ethynyl]-5-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 899629792-[2-(2,6-difluoro-3,5-dimethoxyphenyl)ethyl]-5-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazineYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-[(2,6-difluoro-3,5-dimethoxyphenyl)ethynyl]-5-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazine (490 mg, 1.08 mmol) in tetrahydrofuran (8 mL)/methanol (10 mL), Pd/C (10% w/w, 365 mg, 0.343 mmol) was added. The resulting mixture was stirred under H2 at ambient temperature. After 24 hr, the catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified on silica gel (eluting with 0 to 60% EtOAc in hexanes) to give the desired product (400 mg, 81%). LCMS calculated for C22H19F2N3O4S (M+H)+: m/z=460.1. Found: 460.1.

Workup

  1. customthe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified on silica gel (eluting with 0 to 60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-ac1a900fb78a4732a928a4b2060316ee
Source dataset
uspto-grants-2016_07
Patent number
US09388185B2

Reaction notes

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