p-Toluidine → HCID 21106134, compound

HRID 1354979Notes

Reaction equation

HRID 1354979 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>[C:16]1([CH3:19])[CH:17]=[CH:18][C:13]([NH:12][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][C:3](=[O:4])[CH3:2])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 7813p-ToluidineHCID 62657Potassium Phosphate, TribasicHCID 948182-Bromo-N-phenylacetamide

Product 1

HCID 21106134HCID 21106134, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylCatalyst

Procedure

An oven-dried resealable schlenk tube containing a stir bar was charged with Pd2(dba)3 (4.6 mg, 0.005 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (19.0 mg, 0.04 mmol), 2-bromoacetanilide (107 mg, 0.5 mmol), p-toluidine (80 mg, 0.75 mmol) and K3PO4 (265 mg, 1.25 mmol). The tube was capped with a rubber septum, evacuated and backfilled with argon. tbutanol (1 mL) was added through the septum via syringe. The septum was replaced with a Teflon screw cap. The schlenk tube was sealed and put into a pre-heated oil bath at 110° C. The reaction mixture was stirred for 18 h, allowed to cool down to room temperature and filtered through celite with ethyl acetate. The filtrate was concentrated under reduced pressure. Chromatography on silica gel column with 1:1 hexane:ethyl acetate gave 107 mg (89%) of the title compound as a brown solid.

Workup

  1. additionAn oven-dried resealable schlenk tube containing a stir bar
  2. customThe tube was capped with a rubber septum
  3. customevacuated
  4. additiontbutanol (1 mL) was added through the septum via syringe
  5. customscrew cap
  6. customThe schlenk tube was sealed
  7. customput into a pre-heated oil bath at 110° C
  8. filtrationfiltered through celite with ethyl acetate
  9. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-66a7d8e7e5064662ba9758bc10e01fb4
Source dataset
uspto-grants-2007_05
Patent number
US07223879B2

Reaction notes

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