N-methyl-2-pyrrolidone → HCID 67387471, compound

HRID 906497Notes

Reaction equation

HRID 906497 reaction equation
Cl[C:2]1[CH:7]=[C:6](Br)[CH:5]=[CH:4][C:3]=1[C:9]1[C:22](=[O:23])[N:21]([CH3:24])[C:12]2[NH:13][C:14]3[C:19]([C:11]=2[CH:10]=1)=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3.[C:25]([Cu])#[N:26].[CH3:28][N:29]1C(=O)CCC1>>[C:28]([C:2]1[CH:7]=[C:6]([C:25]#[N:26])[CH:5]=[CH:4][C:3]=1[C:9]1[C:22](=[O:23])[N:21]([CH3:24])[C:12]2[NH:13][C:14]3[C:19]([C:11]=2[CH:10]=1)=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)#[N:29]

Participants

4

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 67387489HCID 67387489, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 67387471HCID 67387471, compound

Procedure

0.6 g of 3-(2-chloro-4-bromophenyl)-1,6-dimethyl-1,9-dihydro-2H-pyrido[2,3-b]indol-2-one is dissolved in 15 ml of NMP. 0.27 g of CuCN is added and then the mixture is heated at reflux for 5 hours. The reaction medium is poured onto CH2Cl2 and washing is carried out with a saturated NaCl solution. Purification is carried out by chromatography on a silica column eluted with an AcOEt/petroleum ether (v/v; 75/25) mixture and then pure AcOEt. The fractions recovered are washed with a 1N HCl solution to remove an NMP residue. 50 mg of the expected compound are obtained in the form of a powder.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 5 hours
  3. additionThe reaction medium is poured onto CH2Cl2
  4. washwashing
  5. customPurification
  6. washeluted with an AcOEt/petroleum ether (v/v; 75/25) mixture
  7. customThe fractions recovered
  8. washare washed with a 1N HCl solution
  9. customto remove an NMP residue

Sources & evidence

ORD record
ord-2a91829297754541b32aeaf01cd69941
Source dataset
uspto-grants-2011_09
Patent number
US08012991B2

Reaction notes

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