Potassium Phosphate, Tribasic → HCID 54671148, compound

HRID 2207825Notes

Reaction equation

HRID 2207825 reaction equation
Cl[C:2]1[C:3]([O:8][CH:9]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]=3)[CH2:10]2)=[N:4][CH:5]=[CH:6][N:7]=1.[CH3:25][C:26]1[CH:31]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:29]=[CH:28][N:27]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:25][C:26]1[CH:31]=[C:30]([C:2]2[C:3]([O:8][CH:9]3[CH2:14][CH2:13][CH2:12][N:11]([C:15]4[CH:24]=[CH:23][C:22]5[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=5)[N:16]=4)[CH2:10]3)=[N:4][CH:5]=[CH:6][N:7]=2)[CH:29]=[CH:28][N:27]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 164142742-Methylpyridine-4-boronic acid pinacol esterHCID 58547693HCID 58547693, compound

Product 1

HCID 54671148HCID 54671148, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of (racemic mixture) 2-(3-((3-chloropyrazin-2-yl)oxy)piperidin-1-yl)quinoline (see PREPARATION P2.3; 340 mg, 1.0 mmol), 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (219 mg, 1.0 mmol) and K3PO4 (424 mg, 2.0 mmol) in 1,4-dioxane (10 mL) and water (2 mL) was added Pd(dppf)Cl2 (73 mg, 0.1 mmol) then the reaction mixture was stirred at 110° C. under N2 atmosphere overnight. The reaction mixture was filtered through CELITE® and washed with CH2Cl2 (30 mL). The filtrate was concentrated and the crude product was purified by silica gel column to give (racemic mixture) 2-(3-((3-(2-methylpyridin-4-yl)pyrazin-2-yl)oxy)piperidin-1-yl)quinoline (200 mg, 0.50 mmol, yield 60%). ESI-MS (M+1): 384 calc. for C23H21N5O 383.

Workup

  1. filtrationThe reaction mixture was filtered through CELITE®
  2. washwashed with CH2Cl2 (30 mL)
  3. concentrationThe filtrate was concentrated
  4. customthe crude product was purified by silica gel column

Sources & evidence

ORD record
ord-446cfe74d4714f7688667dcfa2f66225
Source dataset
uspto-grants-2016_06
Patent number
US09376450B2

Reaction notes

Loading…