Potassium Carbonate → HCID 67974883, compound

HRID 1472685Notes

Reaction equation

HRID 1472685 reaction equation
Cl[C:2]1[C:11]([C:12]([F:15])([F:14])[F:13])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:16][CH3:17])[CH:8]=2)[N:3]=1.[N:18]1[NH:19][N:20]=[N:21][C:22]=1[C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.C([O-])([O-])=O.[K+].[K+]>COCCOCCO.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]>[N:21]1[NH:20][N:19]=[N:18][C:22]=1[C:23]1[CH:28]=[CH:27][C:26]([C:2]2[C:11]([C:12]([F:15])([F:14])[F:13])=[N:10][C:9]3[C:4](=[CH:5][CH:6]=[C:7]([O:16][CH3:17])[CH:8]=3)[N:3]=2)=[CH:25][CH:24]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 46737995[4-(2H-Tetrazol-5-yl)phenyl]boronic acidHCID 53212388HCID 53212388, compound2×

Product 1

HCID 67974883HCID 67974883, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent2×HCID 8134Diethylene Glycol Monomethyl EtherSolvent

Conditions

Temperature
120 °C

Procedure

2-chloro-6-methoxy-3-(trifluoromethyl)quinoxaline (Intermediate 11, 321 mg) was treated with (4-(2H-tetrazol-5-yl)phenyl)boronic acid (256 mg), K2CO3 (338 mg) and PdCl2(dppf) (27 mg) in diethylene glycol methyl ether (3 mL) and water (0.8 mL) in a sealed microwave tube and heated at 120° C. with microwave for 1.5 h. The resultant mixture was diluted with water (20 mL) and acidifed to pH 4 to precipatate the desired product. The solids were collected by filtration, dried under vacuum and trituated with DCM to give 360 mg of gray solid.

Sources & evidence

ORD record
ord-61ec3ee690d748798057d06155b3a0ae
Source dataset
uspto-grants-2015_04
Patent number
US09012646B2

Reaction notes

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