1,2-Dimethoxyethane → Methyl 6-amino-4'-(methylthio)-1,1'-biphenyl-3-carboxylate

HRID 1455646Notes

Reaction equation

HRID 1455646 reaction equation
[F-].[Cs+].COCCOC.[CH3:9][S:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.[NH2:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=1I>CCOC(C)=O.CCCCCC>[NH2:20][C:21]1[C:22]([C:14]2[CH:15]=[CH:16][C:11]([S:10][CH3:9])=[CH:12][CH:13]=2)=[CH:23][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 25953Cesium fluorideHCID 27339594-(Methylthio)phenylboronic acidHCID 4104649Methyl 4-amino-3-iodobenzoate

Product 1

HCID 68952232Methyl 6-amino-4'-(methylthio)-1,1'-biphenyl-3-carboxylate

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Prepared according to the general procedure Coupling-1 (CsF, DME, 20° C.) using [4-(methylthio)phenyl]boronic acid and methyl 4-amino-3-iodo-benzoate as starting material. Flash chromatography (Hexane:EtOAc, 70:30) afforded the title compound as a white solid.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-0adf13041db245d89b9598d772143801
Source dataset
uspto-grants-2009_01
Patent number
US07482456B2

Reaction notes

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