N-methyl-2-pyrrolidone → HCID 67995457, compound
Reaction equation
Br[C:2]1[C:7]2[NH:8][C:9]3[CH:10]=[C:11]([C:15]([O:17][CH3:18])=[O:16])[CH:12]=[CH:13][C:14]=3[C:6]=2[C:5](=[O:19])[NH:4][CH:3]=1.[CH3:20][N:21]1CCCC1=O>>[CH3:18][O:17][C:15]([C:11]1[CH:12]=[CH:13][C:14]2[C:6]3[C:5](=[O:19])[NH:4][CH:3]=[C:2]([C:20]#[N:21])[C:7]=3[NH:8][C:9]=2[CH:10]=1)=[O:16]Participants
Conditions
- Temperature
- 200 °C
Procedure
A stirred mixture of methyl 4-bromo-1-oxo-2,5-dihydro-1H-pyrido[4,3-b]indole-7-carboxylate (0.820 g, 2.55 mmol) and Cuprous cyanide (0.229 g, 2.55 mmol) in N-Methyl-2-pyrrolidinone (25 mL) was heated at 200° C. for 2-4 hours. LC-MS showed complete conversion to the desired product plus minor debrominated product. The reaction mixture was cooled to room temperature then concentrated in vacuo. The residue was slurred in water and filtered. The solid residue was dried overnight under vacuum to give methyl-4-cyano-1-oxo-2,5-dihydro-1H-pyrido[4,3-b]indole-7-carboxylate as a brown solid. [0.672 g product, 2.51 mmol, 98% yield]. The product had an HPLC Retention Time=2.537 min [4 min grad, 10% MeOH/water to 90% MeOH/water, 0.1% TFA, YMC COMBISCREEN® ODS-A, 4.6×50 mm, 220 nM]; LC/MS+1 268.2
Sources & evidence
- ORD record
- ord-6d6cddcf16564c7387305a4bd253be30
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08685969B2
Reaction notes
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