Sodium hydride → N-[6-Cyano-9-(2-methoxy-benzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-isobutyramide
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]1[CH2:10][CH2:9][CH:8]([NH:16][C:17](=[O:21])[CH:18]([CH3:20])[CH3:19])[CH2:7][C:6]2=1)#[N:2].[H-].[Na+].[Na].[CH3:25][O:26][C:27]1[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=1[CH2:29]Cl>CN(C=O)C.O>[C:1]([C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:29][C:28]1[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=1[O:26][CH3:25])[C:11]1[CH2:10][CH2:9][CH:8]([NH:16][C:17](=[O:21])[CH:18]([CH3:19])[CH3:20])[CH2:7][C:6]2=1)#[N:2]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Follow the procedures essentially as described in Example 104, above, using N-(6-cyano-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-isobutyramide (3.38 g, 12 mmol) and treating with sodium hydride (580 mg, 14A mmol). Cool the formed sodium salt in a dry ice/acetonitrile bath and add 2-methoxybenzylchloride (1.84 mL, 13.2 mmol) in DMF (2 mL) at −35 to −30° C. Remove the bath and allow the reaction to warm to ambient temperature over 3 h with stifling. Add water (250 mL) dropwise, cooling in an ice bath while stirring for 30 min. Filter the resulting precipitate and dry under house vacuum at 45° C. for 18 h. Triturate and sonicate the material in diethyl ether for 1.5 h, filter and dry to provide 3.98 g (83%) of an off-white solid.
Workup
- customRemove the bath
- customthe reaction
- filtrationFilter the resulting precipitate
- customdry under house vacuum at 45° C. for 18 h
- customTriturate
- customsonicate the material in diethyl ether for 1.5 h
- filtrationfilter
- customdry
Sources & evidence
- ORD record
- ord-a72de188cfbc408e944e5d5533ac58bf
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935722B2
Reaction notes
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