Potassium Carbonate → HCID 52920397, compound

HRID 1844250Notes

Reaction equation

HRID 1844250 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:10][C@H:9]2[NH:11][CH2:12][C:13]([NH2:15])=[O:14])=[CH:4][CH:3]=1.[F:16][C:17]([F:28])([F:27])[C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1.C([O-])([O-])=O.[K+].[K+]>CC#N.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>[F:16][C:17]([F:28])([F:27])[C:18]1[CH:23]=[C:22]([C:2]2[CH:7]=[CH:6][C:5]([C@@H:8]3[CH2:10][C@H:9]3[NH:11][CH2:12][C:13]([NH2:15])=[O:14])=[CH:4][CH:3]=2)[CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 67114629HCID 67114629, compound

Product 1

HCID 52920397HCID 52920397, compoundYield 80.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A solution of 2-((trans)-2-(4-bromophenyl)cyclopropylamino)acetamide (100 mg, 0.37 mmol, 1 equiv), 3-trifluoro methyl benzene boronic acid (84 mg, 0.44 mmol 1.2 equiv), K2CO3 (152 mg, 1.11 mmol, 3 equiv) in CH3CN+H2O (4:1) (2 mL) was degassed for 30 min with Argon gas, then Pd(PPh3)4 (0.1 equiv) was added and the reaction mixture was heated at reflux temp. for 2 h. After completion, the reaction mixture was poured into ice water (10 mL), extracted with EtOAc (2×10 mL). The combined extracts were washed with water (10 mL), brine (10 mL), dried over anhydrous Na2SO4, filtered and evaporated. The crude residue was purified by prep HPLC to give 2-((trans)-2-(3′-(trifluoromethyl)biphenyl-4-yl)cyclopropylamino)acetamide (100 mg, 80% yield) as a white solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux temp
  3. extractionextracted with EtOAc (2×10 mL)
  4. washThe combined extracts were washed with water (10 mL), brine (10 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude residue was purified by prep HPLC

Sources & evidence

ORD record
ord-97f7939666d24dd384039b13d74855c4
Source dataset
uspto-grants-2015_02
Patent number
US08946296B2

Reaction notes

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