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Cesium carbonate → 3-Cyclopropylamino-5-phenyl-thiophene-2-carboxylic acid methyl ester

HRID 2193922
Notes
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Reaction equation

HRID 2193922 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:9]=1Br)=[O:4].[CH:17]1([NH2:20])[CH2:19][CH2:18]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:9]=1[NH:20][CH:17]1[CH2:19][CH2:18]1)=[O:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 69828CyclopropylamineHCID 634876Binap, (A+-)-HCID 20775762Methyl 3-bromo-5-phenyl-thiophene-2-carboxylate

Product 1

HCID 207757643-Cyclopropylamino-5-phenyl-thiophene-2-carboxylic acid methyl esterYield 22%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Conditions

Temperature
110 °C

Procedure

To a solution of 3-Bromo-5-phenyl-thiophene-2-carboxylic acid methyl ester (250 mg, 0.89 mmol) in toluene (25 ml) was added cyclopropylamine (57 mg, 1.0 mmol), cesium carbonate (382 mg, 1.2 mmol), BINAP (50 mg, 0.08 mmol) and tris(dibenzylidenacetone)dipaladium (0) (38 mg, 0.04 mmol). The reaction mixture was stirred for 16 h at 110° C. in a sealed tube. The mixture was partitioned between toluene (20 mL) and water (20 mL) and the organic layer was separated. The aqueous phase was washed twice with toluene (2×10 mL) and the combined toluene layer was dried (MgSO4), concentrated and the residue was purified by preparative chromatography (10% EtOAc/Hexane) to obtain 52 mg (22%) of 3-Cyclopropylamino-5-phenyl-thiophene-2-carboxylic acid methyl ester. NMR 1H (CDCl3, 400 MHz): 7.67-7.62 ppm (m, 2H, Haro); 7.43-7.32 ppm (m, 3H, Haro); 7.16 ppm (s, 1H, Haro); 3.82 ppm (s, 3H); 2.65 ppm (m, 1H); 0.62 ppm (m, 2H); 0.35 ppm (m, 2H).

Workup

  1. customThe mixture was partitioned between toluene (20 mL) and water (20 mL)
  2. customthe organic layer was separated
  3. washThe aqueous phase was washed twice with toluene (2×10 mL)
  4. dry with materialthe combined toluene layer was dried (MgSO4)
  5. concentrationconcentrated
  6. customthe residue was purified by preparative chromatography (10% EtOAc/Hexane)

Sources & evidence

ORD record
ord-c4b14f320b674a29ae621393d5dc826b
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08329924B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes