Sodium Carbonate → tert-butyl 2-(5-(methoxycarbonyl)thiophen-2-yl)-1H-pyrrole-1-carboxylate

HRID 564228Notes

Reaction equation

HRID 564228 reaction equation
Br[C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][CH:3]=1.[C:11]([O:15][C:16]([N:18]1[CH:22]=[CH:21][CH:20]=[C:19]1B(O)O)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.C(O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:10][O:9][C:7]([C:5]1[S:6][C:2]([C:19]2[N:18]([C:16]([O:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:17])[CH:22]=[CH:21][CH:20]=2)=[CH:3][CH:4]=1)=[O:8]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 605713Methyl 5-bromothiophene-2-carboxylateHCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic Acid

Product 1

HCID 66760515tert-butyl 2-(5-(methoxycarbonyl)thiophen-2-yl)-1H-pyrrole-1-carboxylate

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 86587095Dimethoxyethane ethanol waterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 5-bromothiophene-2-carboxylate (4 g), 1-(tert-butoxycarbonyl)pyrrole-2-boronic acid (3.8 g), dichlorobis (triphenylphosphine)palladium(II) (1.2 g) and 2M sodium carbonate solution (18 mL) in DME/water/ethanol (7/3/2, 200 mL) was heated at 60° C. for 4 hours, cooled and partitioned between ethyl acetate and brine. The extract was washed with water and concentrated, and the concentrate was flash chromatographed on silica gel with 5-40% ethyl acetate in hexane.

Workup

  1. temperaturecooled
  2. custompartitioned between ethyl acetate and brine
  3. washThe extract was washed with water
  4. concentrationconcentrated
  5. customchromatographed on silica gel with 5-40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-a0ce82abe2764de2a3116fb6d3d7ecdd
Source dataset
uspto-grants-2011_11
Patent number
US08067613B2

Reaction notes

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