4-[2-[5,6-Dihydro-5,5-dimethyl-8-[[(trifluoromethyl)sulfonyl]oxy]-2-naphthalenyl]ethynyl]benzoic acid ethyl ester → Ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-(2-pyridyl)naphth-3-yl)ethynyl]benzoate

HRID 265779Notes

Reaction equation

HRID 265779 reaction equation
[CH3:1][C:2]1([CH3:30])[C:11]2[CH:10]=[CH:9][C:8]([C:12]#[C:13][C:14]3[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=3)=[CH:7][C:6]=2[C:5]([C:25]2S[CH:27]=[CH:28][N:29]=2)=[CH:4][CH2:3]1.FC(F)(F)S(O[C:37]1C2C=C(C#CC3C=CC(C(OCC)=O)=CC=3)C=CC=2C(C)(C)C[CH:46]=1)(=O)=O>>[CH3:1][C:2]1([CH3:30])[C:11]2[CH:10]=[CH:9][C:8]([C:12]#[C:13][C:14]3[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=3)=[CH:7][C:6]=2[C:5]([C:25]2[CH:46]=[CH:37][CH:27]=[CH:28][N:29]=2)=[CH:4][CH2:3]1

Participants

3

Reactant 2

HCID 120176384-[2-[5,6-Dihydro-5,5-dimethyl-8-[[(trifluoromethyl)sulfonyl]oxy]-2-naphthalenyl]ethynyl]benzoic acid ethyl ester2×HCID 15430593Ethyl 4-[(5,6-dihydro-5,5-dimethyl-8-(2-thiazolyl)-2-naphthalenyl)ethynyl]benzoate2×

Product 1

HCID 15870721Ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-(2-pyridyl)naphth-3-yl)ethynyl]benzoate

Procedure

Employing the same general procedure as for the preparation of ethyl 4-[(7,8-dihydro-8,8-dimethyl-5-(2-thiazolyl)naphth-2-yl)ethynyl]benzoate (Compound 67), 250.0 mg (0.52 mmol) of ethyl 4-[(5-trifluoromethylsulfonyloxy-7,8-dihydro-8,8-dimethylnaphth-3-yl)ethynyl]benzoate (Compound 66) was converted into the title compound (colorless solid) using 142.4 mg (1.045 mmol) of zinc chloride, 24.1 mg (0.02 mmol) of tetrakis(triphenylphosphine)palladium(0) and 2-lithiopyridine (prepared by the addition of 100.6 mg (0.97 ml, 1.57 mmol) of tert-butyllithium (1.5M solution in pentane) to a cold solution (-78° C.) of 123.8 mg (0.784 mmol) of 2-bromopyridine in 1.0 mL of THF).

Sources & evidence

ORD record
ord-3829714b70bb48008bb175ee2bbc0047
Source dataset
uspto-grants-1997_07
Patent number
US05648514

Reaction notes

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