2-Iodo-4-(methylsulfonyl)-1-propylbenzene → Tert-butyl(4-cyano-2-{[5-(methylsulfonyl)-2-propylphenyl]ethynyl}phenoxy)acetate

HRID 2390163Notes

Reaction equation

HRID 2390163 reaction equation
[C:1]([O:5][C:6](=[O:19])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][C:10]=1[C:17]#[CH:18])([CH3:4])([CH3:3])[CH3:2].I[C:21]1[CH:26]=[C:25]([S:27]([CH3:30])(=[O:29])=[O:28])[CH:24]=[CH:23][C:22]=1[CH2:31][CH2:32][CH3:33]>>[C:1]([O:5][C:6](=[O:19])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][C:10]=1[C:17]#[C:18][C:23]1[CH:24]=[C:25]([S:27]([CH3:30])(=[O:28])=[O:29])[CH:26]=[CH:21][C:22]=1[CH2:31][CH2:32][CH3:33])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 585220032-Iodo-4-(methylsulfonyl)-1-propylbenzene2×HCID 58522073Tert-butyl(4-cyano-2-ethynylphenoxy)acetate2×

Product 1

HCID 58522038Tert-butyl(4-cyano-2-{[5-(methylsulfonyl)-2-propylphenyl]ethynyl}phenoxy)acetate

Procedure

Following the general method as outlined in Intermediate 20, starting from (4-cyano-2-ethynyl-phenoxy)-acetic acid tert-butyl ester (Intermediate 46) and 2-iodo-4-(methylsulfonyl)-1-propylbenzene (Intermediate 62), the title compound was obtained after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record
ord-555b50713def4b41a59ca0aa31161a58
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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