3-Bromo-4-methyl-4,5,7,8-tetrahydro-thieno[2,3-d]azepine-6-carboxylic acid ethyl ester → 3,4-Dimethyl-4,5,7,8-tetrahydro-thieno[2,3-d]azepine-6-carboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH:11]([CH3:13])[C:10]2[C:14](Br)=[CH:15][S:16][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2].[Zn](C)[CH3:19]>O1CCOCC1>[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH:11]([CH3:13])[C:10]2[C:14]([CH3:19])=[CH:15][S:16][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
The product of step (a) (150 mg, 0.47 mmol) was dissolved in 3 mL dioxane and treated with Me2Zn (0.47 mL of 2M in toluene) and Pd(ddf)2Cl2 (11 mg, 0.014 mmol). After heating to 100° C. for 3 hours, the reaction was quenched with water and filtered. The filtrate was partitioned between EtOAc and water (7 mL each). The organic layer was dried over MgSO4 and concentrated to give 92 mg of the sub-title compound, which was used without further purification.
Workup
- customthe reaction was quenched with water
- filtrationfiltered
- customThe filtrate was partitioned between EtOAc and water (7 mL each)
- dry with materialThe organic layer was dried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-eb83049e13254c92a295afbfb90114e7
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08716276B2
Reaction notes
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