Tert-butyl(4-chloro-2-ethynylphenoxy)acetate → HCID 58522051, compound

HRID 2390309Notes

Reaction equation

HRID 2390309 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[CH:52]=[CH:51][C:42]([C:43]([N:45]([CH2:49][CH3:50])[CH2:46][CH2:47][CH3:48])=[O:44])=[C:41]([S:53]([CH:56]([CH3:58])[CH3:57])(=[O:55])=[O:54])[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:52]=[CH:51][C:42]([C:43]([N:45]([CH2:49][CH3:50])[CH2:46][CH2:47][CH3:48])=[O:44])=[C:41]([S:53]([CH:56]([CH3:58])[CH3:57])(=[O:54])=[O:55])[CH:40]=1)([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 3

HCID 56594381Tert-butyl(4-chloro-2-ethynylphenoxy)acetate2×HCID 58521844HCID 58521844, compound2×HCID 58521874{[2-Fluoro-5-(propylsulfonyl)phenyl]ethynyl}trimethyl silane

Product 1

HCID 58522051HCID 58522051, 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 4-bromo-N-ethyl-2-(isopropylsulfonyl)-N-propylbenzamide (Intermediate 259), 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-871a99997fd94f0a99e8f38bcf4f8b1a
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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