Potassium Carbonate → HCID 67974883, compound

HRID 1507381Notes

Reaction equation

HRID 1507381 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, compoundYield 79.1%

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 precipitate the desired product. The solids were collected by filtration, dried under vacuum and triturated with DCM to give 360 mg of gray solid.

Workup

  1. customto precipitate the desired product
  2. filtrationThe solids were collected by filtration
  3. customdried under vacuum
  4. customtriturated with DCM

Sources & evidence

ORD record
ord-454b5a1cc8c542918e38d880acaab6d6
Source dataset
uspto-grants-2015_12
Patent number
US09221810B2

Reaction notes

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