Dichloromethane → HCID 89996095, compound

HRID 1480884Notes

Reaction equation

HRID 1480884 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH:12]([F:14])[F:13])[CH:3]=1.[CH3:15][N:16]1[CH:20]=[C:19](B2OC(C)(C)C(C)(C)O2)[CH:18]=[N:17]1.C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.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]>[F:13][CH:12]([F:14])[O:11][C:4]1[CH:3]=[C:2]([C:19]2[CH:18]=[N:17][N:16]([CH3:15])[CH:20]=2)[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 70558916HCID 70558916, compound

Product 1

HCID 89996095HCID 89996095, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 4-bromo-2-(difluoromethoxy)-1-nitrobenzene (Preparation 215, 174 mg, 0.65 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (150 mg, 0.72 mmol), Pd(dppf)Cl2.DCM (55 mg, 0.068 mmol), Na2CO3 (2M, 0.65 mL, 1.3 mmol) in THF (4 mL) was stirred at 65° C. for 18 hours.

Sources & evidence

ORD record
ord-1c9a5ec80bd74a30874d811a4a51de56
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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