Dimethylformamide → 6-pentafluoroethyl-2,2-bisfluoromethyl-4-(2-pyridyl)-2H-1-benzopyran

HRID 1601410Notes

Reaction equation

HRID 1601410 reaction equation
[F:1][CH2:2][C:3]1([CH2:20][F:21])[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[C:6]2[CH:15]=[C:16](I)[CH:17]=[CH:18][C:5]=2[O:4]1.[F:22][C:23]([F:31])([F:30])[C:24]([F:29])([F:28])C([O-])=O.[K+].CN(C)C=O>[Cu]I.C1(C)C=CC=CC=1>[F:28][C:24]([F:29])([C:16]1[CH:17]=[CH:18][C:5]2[O:4][C:3]([CH2:20][F:21])([CH2:2][F:1])[CH:8]=[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=3)[C:6]=2[CH:15]=1)[C:23]([F:31])([F:30])[F:22]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 218313442,2-bisfluoromethyl-6-iodo-4-(2-pyridyl)-2H-1-benzopyranHCID 23667659Propanoic acid, 2,2,3,3,3-pentafluoro-, potassium salt (1:1)

Product 1

HCID 218313156-pentafluoroethyl-2,2-bisfluoromethyl-4-(2-pyridyl)-2H-1-benzopyranYield 79%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
160 °C

Procedure

A mixture of 1.11 g of 2,2-bisfluoromethyl-6-iodo-4-(2-pyridyl)-2H-1-benzopyran, 1.17 g of potassium pentafluoropropionate, 1.18 g of copper (I) iodide, 20 ml of N,N-dimethylformamide and 7 ml of toluene was stirred at 160° C. under nitrogen gas atmosphere with heating for 3 hours while toluene was distilled off. Ether and water were added thereto and the mixture was filtered using Celite. The mother liquor was extracted with ether. The organic layer was washed with water and dried. The solvent was distilled off and the resultant residue was purified using silica gel column chromatography (developing solution, MeOH:CH2Cl2 =1:99) to obtain 0.86 g of oily 6-pentafluoroethyl-2,2-bisfluoromethyl-4-(2-pyridyl)-2H-1-benzopyran represented by the following formula.

Workup

  1. distillationwas distilled off
  2. additionEther and water were added
  3. filtrationthe mixture was filtered
  4. extractionThe mother liquor was extracted with ether
  5. washThe organic layer was washed with water
  6. customdried
  7. distillationThe solvent was distilled off
  8. customthe resultant residue was purified

Sources & evidence

ORD record
ord-f5f1e91235ef4edbb39b57dd501636f8
Source dataset
uspto-grants-1999_11
Patent number
US05977167

Reaction notes

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