Methyl 4-(((benzyloxy)carbonyl)amino)-5-bromo-2-(4-chlorophenyl)thiophene-3-carboxylate → Methyl 4-(benzyloxycarbonylamino)-2-(4-chlorophenyl)thiophene-3-carboxylate

HRID 1918210Notes

Reaction equation

HRID 1918210 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([C:25]([O:27][CH3:28])=[O:26])=[C:14]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH: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:25]([O:27][CH3:28])=[O:26])=[C:14]([C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=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 58191687Methyl 4-(((benzyloxy)carbonyl)amino)-5-bromo-2-(4-chlorophenyl)thiophene-3-carboxylate

Product 1

HCID 58191256Methyl 4-(benzyloxycarbonylamino)-2-(4-chlorophenyl)thiophene-3-carboxylateYield 64.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22027680Ethanol ethyl acetate methylene chlorideSolvent

Procedure

10% Pd/C (13.7 mg, 13 μmol, 20 mol % Pd) was added to methyl 4-(benzyloxycarbonylamino)-2-(4-chlorophenyl)-5-bromothiophene-3-carboxylate (6) (31.0 mg, 64 μmol) in ethanol:ethyl acetate:dichloromethane (2:1:1, 2.0 mL). The mixture was degassed and placed under H2 (1 atm) and stirred for 4 h. The mixture was filtered through a 0.45 μm syringe filter and concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-50% ethyl acetate in hexane) provided 7 (16.6 mg, 64%) as a solid: LRESIMS m/z 401.9 [M+H]+, calcd. for C20H17Cl1N1O4S1 402.6.

Workup

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

Sources & evidence

ORD record
ord-b220f1df4ab04386871d568b34bc76c9
Source dataset
uspto-grants-2013_12
Patent number
US08618307B2

Reaction notes

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