2-(Dicyclohexylphosphino)biphenyl → HCID 59240555, compound

HRID 42202Notes

Reaction equation

HRID 42202 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1.[CH2:16]([C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]([N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)=[N:25][N:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1CCC(P(C2C(C3C=CC=CC=3)=CC=CC=2)C2CCCCC2)CC1.CC([O-])(C)C.[K+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:16]([C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]([N:33]2[CH2:38][CH2:37][N:36]([C:2]3[N:7]=[CH:6][C:5]([CH2:8][C:9]([N:11]4[CH2:15][CH2:14][CH2:13][CH2:12]4)=[O:10])=[CH:4][CH:3]=3)[CH2:35][CH2:34]2)=[N:25][N:24]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 27342162-(Dicyclohexylphosphino)biphenylHCID 64040231-Benzyl-4-piperazin-1-yl-phthalazineHCID 23665647Potassium tert-butoxideHCID 574716142-(6-Chloro-pyridin-3-yl)-1-pyrrolidin-1-yl-ethanone

Product 1

HCID 59240555HCID 59240555, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of this amide (0.22 g, 1 mmol) and 1-benzyl-4-piperazin-1-yl-phthalazine (0.15 g, 0.5 mmol) in toluene (10 mL) were added (2-biphenyl)dicyclohexyl phosphine (35 mg, 0.1 mmol), Pd(OAc)2 (11 mg, 0.05 mmol) and KOtBu (336 mg, 3 mmol). The mixture was degassed and then heated in a microwave reactor at 90° C. The reaction mixture was cooled to room temperature and filtered. Water was added to the filtrate and extracted with EtOAc. The combined organic layers were washed with water, sat. NaHCO3, brine, dried over Na2SO4, filtered and concentrated.

Workup

  1. customThe mixture was degassed
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered
  4. additionWater was added to the filtrate
  5. extractionextracted with EtOAc
  6. washThe combined organic layers were washed with water, sat. NaHCO3, brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-3d0271881ab04280b77fec1a26ed43cb
Source dataset
uspto-grants-2013_09
Patent number
US08536168B2

Reaction notes

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