Acetonitrile → HCID 67317486, compound

HRID 533254Notes

Reaction equation

HRID 533254 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:3]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21].C1(P(C2CCCCC2)C2C=CC=[CH:34][C:33]=2[C:38]2[C:43](C(C)C)=[CH:42][C:41](C(C)C)=[CH:40][C:39]=2[CH:50]([CH3:52])C)CCCCC1.[C:59]([O-:62])([O-])=O.[Cs+].[Cs+].[C:65](#N)[CH3:66]>C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][N:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2]([C:65]#[C:66][CH2:59][O:62][C:43]3[C:38]4[C:39](=[CH:50][CH:52]=[CH:34][CH:33]=4)[CH:40]=[CH:41][CH:42]=3)=[C:3]2[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 21476954HCID 21476954, compound

Product 1

HCID 67317486HCID 67317486, compound

Reagents, catalysts & solvents 1

HCID 498840Bis(benzonitrile)palladium chlorideCatalyst

Procedure

To a solution of EXAMPLE 101B (3.89 g) in acetonitrile (20 ml) was added Pd(PhCN)2Cl2 (38 mg), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (143 mg), and Cs2CO3 (3.91 g). The mixture was purged with argon and stirred at room temperature for 25 minutes. After this time, 1-(prop-2-ynyloxy)naphthalene (2.2 g) was added to the mixture which was purged with argon again. The mixture was then stirred at 80° C. for 3 hours. The mixture was diluted with ethyl acetate (300 ml) and washed with water, brine and dried over Na2SO4. After filtration, the solvent was concentrated and the residue was loaded on a silica gel column and eluted with 5% ethyl acetate in hexane to give EXAMPLE 102A.

Workup

  1. customThe mixture was purged with argon
  2. additionAfter this time, 1-(prop-2-ynyloxy)naphthalene (2.2 g) was added to the mixture which
  3. customwas purged with argon again
  4. stirringThe mixture was then stirred at 80° C. for 3 hours
  5. additionThe mixture was diluted with ethyl acetate (300 ml)
  6. washwashed with water, brine
  7. dry with materialdried over Na2SO4
  8. filtrationAfter filtration
  9. concentrationthe solvent was concentrated
  10. washeluted with 5% ethyl acetate in hexane
  11. customto give EXAMPLE 102A

Sources & evidence

ORD record
ord-56151a3775164f8ab5de90db80a0f36b
Source dataset
uspto-grants-2014_10
Patent number
US08853209B2

Reaction notes

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