HCID 59164470, compound → HCID 59164455, compound

HRID 1894096Notes

Reaction equation

HRID 1894096 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8](I)[C:7]([CH2:11][F:12])=[CH:6][C:5]=1[NH2:13].[CH:15]([N:18]1[C:22]([Sn](CCCC)(CCCC)CCCC)=[CH:21][CH:20]=[N:19]1)([CH3:17])[CH3:16]>O1CCOCC1.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]>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([C:22]2[N:18]([CH:15]([CH3:17])[CH3:16])[N:19]=[CH:20][CH:21]=2)[C:7]([CH2:11][F:12])=[CH:6][C:5]=1[NH2:13]

Participants

5

Reactant 2

HCID 59164470HCID 59164470, compoundHCID 591645211-Isopropyl-5-tributylstannanyl-1H-pyrazole

Product 1

HCID 59164455HCID 59164455, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-amino-4-fluoromethyl-5-iodo-benzoic acid methyl ester (650 mg, 2.10 mmol) in dioxane (30 mL) were added 1-isopropyl-5-tributylstannanyl-1H-pyrazole (1.01 g, 1.2 equiv) and Pd(dppf)2Cl2 (172 mg, 0.1 equiv) and the resulting mixture was stirred at 90° C. for 18 h. 0.1 equiv of catalyst was added and the mixture was stirred at 90° C. for 24 h. The solvent was removed in vacuo to afford a dark oil. The crude product was purified by flash chromatography (silica gel, EtOAc/hexanes (0:100 to 35:75)) to provide a light yellow solid (243 mg, 40%) (ES-MS: m/z 292.3 [M+H]+, rt 5.31 min).

Workup

  1. stirringthe mixture was stirred at 90° C. for 24 h
  2. customThe solvent was removed in vacuo
  3. customto afford a dark oil
  4. customThe crude product was purified by flash chromatography (silica gel, EtOAc/hexanes (0:100 to 35:75))

Sources & evidence

ORD record
ord-24c016fcbe3a46f58fa11b19ea2ef5cd
Source dataset
uspto-grants-2013_08
Patent number
US08513268B2

Reaction notes

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