2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → HCID 70498313, compound

HRID 1045498Notes

Reaction equation

HRID 1045498 reaction equation
Cl[C:2]1[C:11]2[CH2:10][N:9]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[C:8](=[O:21])[NH:7][C:6]=2[N:5]=[CH:4][CH:3]=1.[Cl:22][C:23]1[CH:31]=[CH:30][C:26]2[O:27][CH2:28][O:29][C:25]=2[C:24]=1[NH2:32].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.CC([O-])(C)C.[Na+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:22][C:23]1[CH:31]=[CH:30][C:26]2[O:27][CH2:28][O:29][C:25]=2[C:24]=1[NH:32][C:2]1[C:11]2[CH2:10][N:9]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[C:8](=[O:21])[NH:7][C:6]=2[N:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 113672535-Chloro-1,3-benzodioxol-4-amineHCID 23676156Sodium t-butoxideHCID 669262915-chloro-3-[(4-methoxyphenyl)methyl]-1H,2H,3H,4H-pyrido[2,3-d]pyrimidin-2-one

Product 1

HCID 70498313HCID 70498313, compoundYield 35%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
120 °C

Procedure

1 (69 mg, 0.23 mmol), 5-chloro-1,3-benzodioxol-4-amine (47 mg, 0.27 mmol), Pd(OAc)2 (2.5 mg, 0.01 mmol), X-Phos (11 mg, 0.02 mmol), and NaOtBu (65 mg, 0.68 mmol) were suspended in anhydrous dioxane (2 mL), and stirred in a microwave at 120° C. for 150 min. The crude product was purified directly via HPLC to provide 101 (35% yield). LC-MS (M+H=439, obsd.=439).

Workup

  1. customThe crude product was purified directly via HPLC

Sources & evidence

ORD record
ord-de6d3dfbaf8845ec93f6057f4fe25119
Source dataset
uspto-grants-2013_10
Patent number
US08569295B2

Reaction notes

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