Hydrochloric Acid → HCID 178487824, compound

HRID 55780

Reaction equation

HRID 55780 reaction equation
Cl[C:2]1[C:11]([CH3:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1.[NH:15]1[C:19]([C:20]2[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=2)=[N:18][N:17]=[N:16]1.C([O-])([O-])=O.[K+].[K+].COCCOCCO.Cl>[OH-].[Na+].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].O>[NH:18]1[C:19]([C:20]2[CH:25]=[CH:24][C:23]([C:2]3[C:11]([CH3:12])=[CH:10][C:9]4[C:4](=[CH:5][CH:6]=[C:7]([O:13][CH3:14])[CH:8]=4)[N:3]=3)=[CH:22][CH:21]=2)=[N:15][N:16]=[N:17]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8134Diethylene Glycol Monomethyl EtherHCID 11430Potassium CarbonateHCID 49146642-Chloro-6-methoxy-3-methylquinolineHCID 178514828HCID 178514828, compound

Product 1

HCID 178487824HCID 178487824, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 2-chloro-6-methoxy-3-methylquinoline (100 mg, 0.482 mmol), 4-(1H-tetrazol-5-yl)phenylboronic acid (91.2 mg, 0.482 mmol), K2CO3 (199 mg, 1.45 mmol), and PdCl2(dppf) (17.6 mg, 0.024 mmol) was added 7 mL of DEGME and 3 mL of H2O under argon. The mixture was stirred at 150° C. in a microwave reactor for 1.5 hours. The crude mixture was diluted with 1N NaOH (10 mL) and slowly acidified to a pH of 4.0 using conc. HCl. The solids were filtered to yield 128 mg (84% yield) of desired product.

Workup

  1. filtrationThe solids were filtered

Sources & evidence

ORD record
ord-4827d6c016174071b5a561081304ea89
Source dataset
uspto-grants-2016_09
Patent number
US09433618B2

Linked notes

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