Dichloromethane → 5-(Prop-1-en-2-yl)-2-(trifluoromethyl)pyridine

HRID 1438380Notes

Reaction equation

HRID 1438380 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([F:11])([F:10])[F:9])=[N:6][CH:7]=1.[C:12]([B-](F)(F)F)([CH3:14])=[CH2:13].[K+].C(Cl)Cl.C(N(CC)CC)C>C(O)CC.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]>[C:12]([C:2]1[CH:3]=[CH:4][C:5]([C:8]([F:11])([F:10])[F:9])=[N:6][CH:7]=1)([CH3:14])=[CH2:13]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 27611975-Bromo-2-(trifluoromethyl)pyridineHCID 23670158Potassium (prop-1-en-2-yl)trifluoroborate

Product 1

HCID 576623365-(Prop-1-en-2-yl)-2-(trifluoromethyl)pyridineYield 59%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 10311-PropanolSolvent

Procedure

A mixture of 5-bromo-2-(trifluoromethyl)pyridine (452 mg, 2.0 mmol), potassium isopropenyltrifluoroborate (355 mg, 2.4 mmol), PdCl2(dppf).CH2Cl2 (82 mg, 0.1 mmol) and triethylamine (0.28 ml, 2.0 mmol) in n-propanol (20 ml) was treated in the same procedure as described in Example 10B. The crude residue was applied to a silica gel chromatography column and eluted with a volume mixture of hexane and EtOAc (20/1) to afford 219 mg (59% yield) of the title compound as a colorless oil.

Workup

  1. washeluted with a volume mixture of hexane and EtOAc (20/1)

Sources & evidence

ORD record
ord-f6ab408b0c43497e99c7b702818ab630
Source dataset
uspto-grants-2009_11
Patent number
US07622589B2

Reaction notes

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