Ethynylpyridine → HCID 86599493, compound

HRID 855116Notes

Reaction equation

HRID 855116 reaction equation
I[C:2]1[CH:3]=[C:4]([O:21][C:22]([F:25])([F:24])[F:23])[CH:5]=[C:6]2[C:11]=1[O:10][CH:9]([C:12]([F:15])([F:14])[F:13])[C:8]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:7]2.[N:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:32]#[CH:33]>C1(C)C=CC=CC=1.[Cu]I.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(Cl)Cl>[N:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:32]#[C:33][C:2]1[CH:3]=[C:4]([O:21][C:22]([F:24])([F:23])[F:25])[CH:5]=[C:6]2[C:11]=1[O:10][CH:9]([C:12]([F:14])([F:15])[F:13])[C:8]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:7]2

Participants

6

Reactant 2

HCID 137268EthynylpyridineHCID 86599457ethyl 8-iodo-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Product 1

HCID 86599493HCID 86599493, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418807HCID 178418807, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of ethyl 8-iodo-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate prepared as in Example 21a, Step 2 (1.00 g, 2.07 mmole), 2-pyridylacetylene (419 uL, 4.15 mmole), CuI (39 mg, 0.207 mmole), PdCl2(dppf)2-CH2Cl2 (169 mg, 0.207 mmole) and TEA (0.866 mL, 6.21 mmole) in anhydrous toluene (10 mL) was stirred at room temperature for 5 days under a N2 atmosphere. The mixture was then diluted with hexanes and purified by silica chromatography (0% to 75% EtOAc:hexanes gradient) to give 0.73 g (77% yield) the title product as a pale yellow crystalline solid: ESHRMS m/z 458.0849 (M+H, C21H14F6NO4, Calc'd 458.0822).

Workup

  1. custompurified by silica chromatography (0% to 75% EtOAc:hexanes gradient)

Sources & evidence

ORD record
ord-a845c58339c643d3b9f56784ba1f5ba5
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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