3-bromo-N,N-dimethylbenzamide → HCID 58521976, compound

HRID 2390239

Reaction equation

HRID 2390239 reaction equation
[C:1]([O:5][C:6](=[O:18])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]#[CH:17])([CH3:4])([CH3:3])[CH3:2].Br[C:20]1[CH:21]=[C:22]([CH:28]=[CH:29][CH:30]=1)[C:23]([N:25]([CH3:27])[CH3:26])=[O:24]>>[C:1]([O:5][C:6](=[O:18])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]#[C:17][C:29]1[CH:30]=[CH:20][CH:21]=[C:22]([C:23]([N:25]([CH3:27])[CH3:26])=[O:24])[CH:28]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 33358263-bromo-N,N-dimethylbenzamide2×HCID 56594381HCID 56594381, compound2×

Product 1

HCID 58521976HCID 58521976, compound

Procedure

Following the general method as outlined in Intermediate 20, starting from (4-chloro-2-ethynyl-phenoxy)-acetic acid tert-butyl ester (Intermediate 3) and 3-bromo-N,N-dimethylbenzamide (Intermediate 180), 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-7e477b5d4ae94c7f8f66875eaa2441cd
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Linked notes

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