Tert-butyl(4-chloro-2-ethynylphenoxy)acetate → HCID 58521910, compound

HRID 2390285Notes

Reaction equation

HRID 2390285 reaction equation
FC1C=CC(S(CCC)(=O)=O)=CC=1C#C[Si](C)(C)C.[C:20]([O:24][C:25](=[O:37])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=1[C:35]#[CH:36])([CH3:23])([CH3:22])[CH3:21].Br[C:39]1[C:44]([CH3:45])=[CH:43][C:42]([NH:46][C:47](=[O:49])[CH3:48])=[C:41]([S:50]([CH2:53][CH2:54][CH3:55])(=[O:52])=[O:51])[CH:40]=1>>[C:20]([O:24][C:25](=[O:37])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=1[C:35]#[C:36][C:39]1[CH:40]=[C:41]([S:50]([CH2:53][CH2:54][CH3:55])(=[O:52])=[O:51])[C:42]([NH:46][C:47](=[O:49])[CH3:48])=[CH:43][C:44]=1[CH3:45])([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 3

HCID 56594381Tert-butyl(4-chloro-2-ethynylphenoxy)acetate2×HCID 58521825HCID 58521825, compound2×HCID 58521874{[2-Fluoro-5-(propylsulfonyl)phenyl]ethynyl}trimethyl silane

Product 1

HCID 58521910HCID 58521910, compound

Procedure

Following the general method as outlined in Intermediate 107, starting from (4-chloro-2-ethynyl-phenoxy)-acetic acid tert-butyl ester (Intermediate 3) and N-[4-Bromo-5-methyl-2-(propane-1-sulfonyl)-phenyl]-acetamide (Intermediate 230), the title compound was obtained as a brown sticky solid after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record
ord-be29b51c9dcf4173a69487a4770088dc
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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