Water → HCID 11773104, compound

HRID 643688Notes

Reaction equation

HRID 643688 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6](Br)[CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10].[CH:17]1([NH:20][C:21](=[O:30])[C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[C:24](I)[CH:23]=2)[CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:17]1([NH:20][C:21]([C:22]2[CH:27]=[C:26]([C:6]3[CH:5]=[CH:4][C:3]([C:9](=[O:10])[C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[C:2]([NH2:1])[CH:7]=3)[C:25]([CH3:28])=[CH:24][CH:23]=2)=[O:30])[CH2:18][CH2:19]1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 4149946(2-Amino-4-bromophenyl)(phenyl)methanoneHCID 21914546N-Cyclopropyl-3-iodo-4-methylbenzamide

Product 1

HCID 11773104HCID 11773104, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
95 °C

Procedure

To a solution the (2-Amino-4-bromo-phenyl)-phenyl-methanone (276 mg, 1.0 mmol) and N-Cyclopropyl-3-iodo-4-methyl-benzamide (301 mg, 1.0 mmol) in 5 mL of methyl sulfoxide was added potassium carbonate (276 mg, 2.0 mmol) and followed by Pd(PPh3)4 (58 mg, 0.05 mmol). After the reaction mixture was stirred at 95° C. for 4 hours, the reaction mixture was allowed to cool to room temperature and 10 mL of water was added to the mixture. The resulting mixture was extracted with ethyl acetate (3×50 mL). The combined organic layers washed with water (10 mL) and brine (10 mL), dried over MgSO4, and the solvents were evaporated. The residue was purified by chromatography (hexanes:ethyl acetate=1:1) to give the desired compound as a colorless solid (180 mg, 49%).

Workup

  1. temperatureto cool to room temperature
  2. extractionThe resulting mixture was extracted with ethyl acetate (3×50 mL)
  3. washThe combined organic layers washed with water (10 mL) and brine (10 mL)
  4. dry with materialdried over MgSO4
  5. customthe solvents were evaporated
  6. customThe residue was purified by chromatography (hexanes:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-5424cc6b2e0d42fc8622fc146ddef4e7
Source dataset
uspto-grants-2010_04
Patent number
US07700622B2

Reaction notes

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