Methyl 4-(benzyloxycarbonylamino)-5-bromo-2-(5-methoxypyrazin-2-yl)thiophene-3-carboxylate → Methyl 4-(benzyloxycarbonylamino)-2-(5-methoxypyrazin-2-yl)thiophene-3-carboxylate

HRID 1918213Notes

Reaction equation

HRID 1918213 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([C:26]([O:28][CH3:29])=[O:27])=[C:14]([C:18]2[CH:23]=[N:22][C:21]([O:24][CH3:25])=[CH:20][N:19]=2)[S:15][C:16]=1Br)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.C(OCC)(=O)C.ClCCl.[Pd]>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([C:26]([O:28][CH3:29])=[O:27])=[C:14]([C:18]2[CH:23]=[N:22][C:21]([O:24][CH3:25])=[CH:20][N:19]=2)[S:15][CH:16]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 58191419Methyl 4-(benzyloxycarbonylamino)-5-bromo-2-(5-methoxypyrazin-2-yl)thiophene-3-carboxylate

Product 1

HCID 58191520Methyl 4-(benzyloxycarbonylamino)-2-(5-methoxypyrazin-2-yl)thiophene-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22027680Ethanol ethyl acetate methylene chlorideSolvent

Procedure

10% Pd/C is added to methyl 4-(benzyloxycarbonylamino)-5-bromo-2-(5-methoxypyrazin-2-yl)thiophene-3-carboxylate (157) in ethanol:ethyl acetate:dichloromethane (2:1:1). The mixture is degassed and placed under H2 (1 atm) and stirred for 4 h. The mixture is filtered through a 0.45 μm syringe filter and concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-50% ethyl acetate in hexane) provides 158.

Workup

  1. customThe mixture is degassed
  2. filtrationThe mixture is filtered through a 0.45 μm syringe
  3. filtrationfilter
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6e0cc6a2945146218d36960dc266ca73
Source dataset
uspto-grants-2013_12
Patent number
US08618307B2

Reaction notes

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