(5-Methoxypyrazin-2-YL)boronic acid → Methyl 4-(benzyloxycarbonylamino)-5-bromo-2-(5-methoxypyrazin-2-yl)thiophene-3-carboxylate

HRID 1918212Notes

Reaction equation

HRID 1918212 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([C:19]([O:21][CH3:22])=[O:20])=[C:14](Br)[S:15][C:16]=1[Br:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][O:24][C:25]1[N:26]=[CH:27][C:28](B(O)O)=[N:29][CH:30]=1>C(O)C.O.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([C:19]([O:21][CH3:22])=[O:20])=[C:14]([C:28]2[CH:27]=[N:26][C:25]([O:24][CH3:23])=[CH:30][N:29]=2)[S:15][C:16]=1[Br:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 45785501(5-Methoxypyrazin-2-YL)boronic acidHCID 58191482Methyl 4-(((benzyloxy)carbonyl)amino)-2,5-dibromothiophene-3-carboxylate

Product 1

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

Reagents, catalysts & solvents 2

HCID 10340Sodium CarbonateSolventHCID 86587398Ethanol toluene waterSolvent

Conditions

Temperature
80 °C

Procedure

Palladium tetrakis-triphenylphosphine is added to a degassed solution of dibromide 155 and 5-methoxypyrazin-2-ylboronic acid 156 in ethanol: water:toluene (2:1:1) and sodium carbonate. The resulting mixture is heated under N2 and stirred for 1 h at 80° C. The mixture is then cooled 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 157.

Workup

  1. temperatureThe resulting mixture is heated under N2
  2. temperatureThe mixture is then cooled
  3. filtrationfiltered through a 0.45 μm syringe
  4. filtrationfilter
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ff377f6bd6ae401d9f5b6a5cd8c45968
Source dataset
uspto-grants-2013_12
Patent number
US08618307B2

Reaction notes

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