Sodium Carbonate → HCID 118046190, compound

HRID 596066Notes

Reaction equation

HRID 596066 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([F:18])[CH:9]=2)=[CH:6][C:5](B2OC(C)(C)C(C)(C)O2)=[CH:4][N:3]=1.F[CH:29](F)[N:30]1[CH:34]=[C:33](I)[C:32](C)=[N:31]1.C([O-])([O-])=O.[Na+].[Na+].[O-]S([O-])(=O)=O.[Na+].[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].CCOC(C)=O.COCCOC>[NH2:1][C:2]1[C:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([F:18])[CH:9]=2)=[CH:6][C:5]([C:33]2[CH:32]=[N:31][N:30]([CH3:29])[CH:34]=2)=[CH:4][N:3]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 24436Sodium SulfateHCID 463183071-(Difluoromethyl)-4-iodo-3-methyl-1H-pyrazoleHCID 123330616HCID 123330616, compound

Product 1

HCID 118046190HCID 118046190, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of crude methyl 4-(2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-2-fluorobenzoate (712 mg, 1.912 mmol), 1-(difluoromethyl)-4-iodo-3-methyl-1H-pyrazole (740 mg, 2.87 mmol), PdCl2(dppf) (70.0 mg, 0.096 mmol), DME (7.899 mL), and 2M Na2CO3 (3.95 mL) was heated at 100° C. overnight. After adding Na2SO4 followed by dilution with EtOAc, the reaction mixture was filtered off and the resulting volatile materials were concentrated in vacuo. The crude product was purified by flash chromatography eluting with 0-100% of EtOAc in DCM. LCMS (m/z): 491.1 (MH+), 0.64 min

Workup

  1. filtrationthe reaction mixture was filtered off
  2. concentrationthe resulting volatile materials were concentrated in vacuo
  3. customThe crude product was purified by flash chromatography
  4. washeluting with 0-100% of EtOAc in DCM
  5. custom491.1 (MH+), 0.64 min

Sources & evidence

ORD record
ord-82a1d98e52b84479b39aa76c01f42891
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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