Dimethylamine → 1-(6-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)pyridin-3-yl)-N,N-dimethylmethanamine
Reaction equation
[F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][N:15]=3)[S:13][C:6]=12.[CH3:29][NH:30][CH3:31].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:15]=[CH:16][C:17]([CH2:18][N:30]([CH3:31])[CH3:29])=[CH:20][CH:21]=3)[S:13][C:6]=12Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 400 (360 mg, 0.91 mmol) and dimethylamine (2M THF solution, 550 μL, 1.09 mmol) in DCM (10 mL) was stirred at room temperature for 10 min. It was then treated with NaBH(OAc)3 (270 mg, 1.27 mmol) and stirred at room temperature overnight. The reaction mixture was diluted with DCM (30 mL) and washed with saturated NaHCO3 solution (30 mL), dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash chromatography using the gradient 10-30% MeOH in DCM as an eluent, to provide title compound 402 (321 mg, 83% yield). MS (m/z): (M+1) 425.1 (100%).
Workup
- stirringstirred at room temperature overnight
- washwashed with saturated NaHCO3 solution (30 mL)
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by flash chromatography
Sources & evidence
- ORD record
- ord-d6d68644563846c9a66b146450cdd9a2
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093264B2
Reaction notes
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