Cesium carbonate → HCID 89741487, compound

HRID 2278382Notes

Reaction equation

HRID 2278382 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][O:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=1)=[O:5])[CH3:2].[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][C:26]1([CH3:32])[CH3:31])=[O:24])([CH3:21])([CH3:20])[CH3:19].C1(C2C=CC=CC=2)C=CC=CC=1P(C1CCCCC1)C1CCCCC1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1>[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][N:28]([C:14]2[CH:15]=[CH:16][C:11]([C:10]3[O:9][CH:8]=[N:7][C:6]=3[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:12][CH:13]=2)[CH2:27][C:26]1([CH3:32])[CH3:31])=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 299224001,1-Dimethylethyl 2,2-dimethyl-1-piperazinecarboxylateHCID 61636738Ethyl 5-(4-iodophenyl)oxazole-4-carboxylate

Product 1

HCID 89741487HCID 89741487, compoundYield 43.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 5-(4-iodo-phenyl)-oxazole-4-carboxylic acid ethyl ester (11.0 g, 32 mmol) in dry toluene (300 mL) was added 2,2-dimethyl-piperazine-1-carboxylic acid tert-butyl ester (7.53 g, 35.2 mmol), Pd(AcO)2 (580 mg, 2.56 mmol), biphenyl-2-yldicyclohexylphosphine (0.9 g, 2.56 mmol) and Cs2CO3 (20.7 g, 64 mmol) under a nitrogen atmosphere at room temperature. The mixture was heated to 80° C. and stirred for 24 hrs. The solution was allowed to cool to room temperature and was then partitioned between water and EtOAc. The organic phase was dried over Na2SO4 and the solvent was removed to give the crude product. It was purified by silica gel column chromatography (PE/EtOAc=40/1˜10/1 to recover unreacted starting material; PE/EtOAc=8/1˜5/1 to yield the title compound (6.0 g, 43%) as a yellow solid.

Workup

  1. temperatureto cool to room temperature
  2. customwas then partitioned between water and EtOAc
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customthe solvent was removed
  5. customto give the crude product
  6. customIt was purified by silica gel column chromatography (PE/EtOAc=40/1˜10/1
  7. customto recover unreacted

Sources & evidence

ORD record
ord-b0bffed223c94c898a953b18abd9d2e8
Source dataset
uspto-grants-2015_09
Patent number
US09133180B2

Reaction notes

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