Potassium Carbonate → HCID 58154664, compound

HRID 2359401Notes

Reaction equation

HRID 2359401 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([NH:12][CH2:13][C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[N:20]1[CH:25]=[CH:24][CH:23]=[C:22](B(O)O)[CH:21]=1.C([O-])([O-])=O.[K+].[K+]>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].O1CCOCC1.O>[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[C:5]([NH:12][CH2:13][C:14]4[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=4)[CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH:21]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 58154530HCID 58154530, compound

Product 1

HCID 58154664HCID 58154664, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A mixture of 2-chloro-N-(pyridin-3-ylmethyl)quinolin-8-amine (160 mg, 0.59 mmol), 3-pyridylboronic acid (111 mg, 0.9 mmol), PdCl2(dppf).CH2Cl2 complex (53 mg, 0.06 mmol), K2CO3 (248 mg, 1.8 mmol) and dioxane/H2O (5:1, 6 ml) was stirred at 80° C. for 3 h under N2. The reaction was filtered, concentrated and purified by prepTLC (4:1 pentane/ethyl acetate) to give 2-(pyridin-3-yl)-N-(pyridin-3-ylmethyl)quinolin-8-amine as a yellow solid (139 mg, yield 75%). MS (ESI) calcd for C20H16N4 (m/z): 312.14. found: 313 [M+1].

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. custompurified by prepTLC (4:1 pentane/ethyl acetate)

Sources & evidence

ORD record
ord-2779f07398a642739b4c443c250b6ed9
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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