Ethyl Acetate → N-(6-chloro-4-methyl-9H-beta-carbolin-8-yl)-nicotinamide

HRID 12223

Reaction equation

HRID 12223 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH2:15])[CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[C:6]([CH3:16])[C:5]2=1.Cl.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[N:21][CH:20]=1.CCOC(C)=O>N1C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH:15][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[N:21][CH:20]=3)[CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[C:6]([CH3:16])[C:5]2=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 593375486-chloro-4-methyl-9H-beta-carbolin-8-ylamine

Product 1

HCID 11302139N-(6-chloro-4-methyl-9H-beta-carbolin-8-yl)-nicotinamideYield 8.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1049PyridineSolvent

Procedure

A solution of 6-chloro-4-methyl-9H-β-carbolin-8-ylamine (43 mg, 0.19 mmol) in pyridine (4 ml) was stirred at RT under an argon atmosphere. Nicotinoyl chloride hydrochloride (40 mg, 0.22 mmol) was added thereto and the reaction mixture was stirred for 12 hr. The solution was diluted with H2O (5 ml) and poured into a separatory funnel containing H2O (5 ml) and EtOAc (25 ml). The reaction mixture was shaken and the layers were separated. The aqueous layer was extracted with EtOAc (2×25 ml). The combined organic layers were washed with a saturated sodium bicarbonate solution (15 ml), followed by brine, then dried over MgSO4, filtered, and concentrated to yield N-(6-chloro-4-methyl-9H-β-carbolin-8-yl)-nicotinamide (5.2 mg) as an orange viscous oil.

Workup

  1. additionpoured into a separatory funnel
  2. stirringThe reaction mixture was shaken
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with EtOAc (2×25 ml)
  5. washThe combined organic layers were washed with a saturated sodium bicarbonate solution (15 ml)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6ae8c9d0d8654400b65d536d16c21f9b
Source dataset
uspto-grants-2010_06
Patent number
US07727985B2

Linked notes

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