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

HRID 1052243Notes

Reaction equation

HRID 1052243 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:11]=[CH:12]/[C:13]2[N:14]=[C:15]3[CH:21]=[CH:20][N:19]([S:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)(=[O:24])=[O:23])[C:16]3=[N:17][CH:18]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.CO>O1CCCC1.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]2[N:14]=[C:15]3[CH:21]=[CH:20][N:19]([S:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)(=[O:24])=[O:23])[C:16]3=[N:17][CH:18]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 899631882-[(E)-2-(3,5-dimethoxyphenyl)vinyl]-5-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 899633512-[2-(3,5-dimethoxyphenyl)ethyl]-5-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazineYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-[(E)-2-(3,5-dimethoxyphenyl)vinyl]-5-(phenylsulfonyl)-5H-pyrrolo[2,3-b]pyrazine (1.10 g, 2.61 mmol) in tetrahydrofuran (8 mL)/methanol (10 mL), was added Pd/C (10% w/w, 580 mg, 0.545 mmol). The resulted mixture was stirred under H2 (45 psi) at ambient temperature. After 24 hours, the palladium catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure to afford the desired product (1.05 g, 90%), which was used directly in the next step without further purification. LCMS calculated for C22H22N3O4S (M+H)+: m/z=424.2. Found: 424.2; 1H NMR (400 MHz, CDCl3): δ 8.18-8.15 (m, 3H), 7.97 (d, J=4.4 Hz, 1H), 7.63-7.59 (m, 1H), 7.53-7.48 (m, 2H), 6.80 (d, J=4.4 Hz, 1H), 6.34 (d, J=2.0 Hz, 2H), 6.30 (t, J=2.4 Hz, 1H), 3.73 (s, 6H), 3.19-3.15 (m, 2H), 3.02-2.98 (m, 2H) ppm.

Workup

  1. customthe palladium catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fc1b8c3dcd6a4f71bc9bfb3330bb5bbd
Source dataset
uspto-grants-2016_07
Patent number
US09388185B2

Reaction notes

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