Acetic Acid → 4-((7-Chlorothieno[3,2-b]pyridin-2-yl)methyl)morpholine
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([CH:11]=O)[S:10][C:3]=12.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO.CO.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([CH2:11][N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[S:10][C:3]=12Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of aldehyde 14 (scheme 3) (316 mg, 1.6 mmol) and morpholine (0.15 ml, 1.52 mmol) in MeOH (20 mL) was added acetic acid (0.88 ml, 15 mmol), followed by sodium cyanoborohydride (105 mg, 1.67 mmol). The resultant mixture was allowed to stir for 18 h, quenched with saturated aqueous potassium carbonate solution (5 mL), evaporated under reduced pressure and the residue was partitioned between EtOAc and water. The organic phase was dried over anhydrous sodium sulfate, concentrated to dryness and the remained solid was purified by column chromatography, eluents EtOAc/hexane (30:70), then MeOH/EtOAc (1:99), to afford the title compound 131 (120 mg, 29% yield). MS (m/z) 269.0/271.0 (M+H).
Workup
- customquenched with saturated aqueous potassium carbonate solution (5 mL)
- customevaporated under reduced pressure
- customthe residue was partitioned between EtOAc and water
- dry with materialThe organic phase was dried over anhydrous sodium sulfate
- concentrationconcentrated to dryness
- customthe remained solid was purified by column chromatography, eluents EtOAc/hexane (30:70)
Sources & evidence
- ORD record
- ord-1d9881f0d1e94e899a581f8824e450c0
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08470850B2
Reaction notes
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