2-(Dicyclohexylphosphino)biphenyl → HCID 11248201, compound

HRID 2415396Notes

Reaction equation

HRID 2415396 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]3[C:14]4[NH:15][C:16]5[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=5[C:22](=[O:23])[C:13]=4[CH2:12][NH:11]3)=[CH:9][C:4]=2[CH2:3][CH2:2]1.Cl[C:25]1[CH:30]=[CH:29][C:28]([C:31]2[N:32]([CH3:36])[CH:33]=[N:34][CH:35]=2)=[CH:27][N:26]=1.C1(C2C=CC=CC=2)C=CC=CC=1P(C1CCCCC1)C1CCCCC1.CC([O-])(C)C.[Na+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]3[C:14]4[NH:15][C:16]5[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=5[C:22](=[O:23])[C:13]=4[CH2:12][N:11]3[C:25]3[CH:30]=[CH:29][C:28]([C:31]4[N:32]([CH3:36])[CH:33]=[N:34][CH:35]=4)=[CH:27][N:26]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 27342162-(Dicyclohexylphosphino)biphenylHCID 12993017HCID 12993017, compoundHCID 22640298HCID 22640298, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 11248201HCID 11248201, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

3-(2,3-dihydro-benzofuran-5-yl)-1,2,3,4-tetrahydro-pyrrolo[3,4-b]quinolin-9-one (0.127 g, 0.372 mmol), 2-chloro-5-(3-methyl-3H-imidazol-4-yl)-pyridine (0.06 g, 0.31 mmol), Pd(OAc)2 (3.5 mg, 0.0155 mmol), biphenyl-2-yl-dicyclohexyl-phosphane (5.43 mg, 0.0155 mmol) and NaOtBu (0.104 g, 1.085 mmol) were stirred in 1,4-dioxane (0.6 mL) at 90° C. Purification by preparative TLC (5% MeOH in CH2Cl2) yielded the product as yellow solid.

Workup

  1. customPurification by preparative TLC (5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-9a766f26b947495babac1e02a43263f4
Source dataset
uspto-grants-2004_11
Patent number
US06818646B2

Reaction notes

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