Dichloromethane → HCID 11965784, compound

HRID 1441648Notes

Reaction equation

HRID 1441648 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8](I)[C:7]([C:11]([F:14])([F:13])[F:12])=[CH:6][C:5]=1[NH2:15].[N:17]1[CH:22]=[C:21](B(O)O)[CH:20]=[N:19][CH:18]=1.C(Cl)Cl.C([O-])([O-])=O.[Cs+].[Cs+]>COCCOC.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:16])[C:4]1[CH:9]=[C:8]([C:21]2[CH:22]=[N:17][CH:18]=[N:19][CH:20]=2)[C:7]([C:11]([F:14])([F:13])[F:12])=[CH:6][C:5]=1[NH2:15]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 53436880Methyl 2-amino-5-iodo-4-(trifluoromethyl)benzoate

Product 1

HCID 11965784HCID 11965784, compoundYield 41%

Reagents, catalysts & solvents 2

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

Procedure

To a solution of 2-amino-5-iodo-4-trifluoromethyl-benzoic acid methyl ester (1.5 g, 4.35 mmol) in DME (50 mL) were added pyrimidine-5-boronic acid (538.7 mg, 4.35 mmol), Pd(dppf)Cl2.CH2Cl2 (355 mg, 0.43 mmol), Cs2CO3 (2.8 g, 8.7 mmol) and the resultant mixture was stirred at reflux temperature for 36 h. The solvent was removed in vacuo and the residue was purified by flash chromatography (120 g silica gel, hexanes→EtOAc/hexanes (3:7 to 1:1)) to furnish the title product (528 mg, 41%) as a beige solid. API-ES: m/z 298 [M+H]+, rt 4.06 min.

Workup

  1. temperatureat reflux temperature for 36 h
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by flash chromatography (120 g silica gel, hexanes→EtOAc/hexanes (3:7 to 1:1))

Sources & evidence

ORD record
ord-e23132dc55b24973b78ae9d2413db183
Source dataset
uspto-grants-2010_02
Patent number
US07655666B2

Reaction notes

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