Carbazole → HCID 59638318, compound

HRID 1037516Notes

Reaction equation

HRID 1037516 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10](Br)[N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH:13]1[C:25]2[NH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]=2[CH:16]=[CH:15][CH:14]=1.C1O[CH2:42][CH2:41]OCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+]>ClC1C=CC=CC=1Cl>[CH:22]1[C:23]2[N:24]([C:2]3[CH:3]=[C:4]([CH:9]=[C:10]([N:24]4[C:42]5[CH:41]=[CH:14][CH:15]=[CH:16][C:17]=5[C:18]5[C:23]4=[CH:22][CH:21]=[CH:20][CH:19]=5)[N:11]=3)[C:5]([O:7][CH3:8])=[O:6])[C:25]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18]=2[CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 6854CarbazoleHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 19261659Methyl 2,6-dibromopyridine-4-carboxylate

Product 1

HCID 59638318HCID 59638318, compound

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

To a solution of methyl 2,6-dibromo-isonicotinate (5.0 g, 16.95 mmol) (YZ_I-131), carbazole (6.0 g, 35.88 mmol) Cu (15.0 g, 236.04 mmol) and 18-crown-6 (0.1 g, 0.38 mmol) in 1,2-dichlorobenzene (50.0 ml) was added potassium carbonate (20.0 g, 144.71 mmol) under nitrogen and stirring. The reaction was carried out at 180° C. for 9 hours. After cooling, the reaction mixture was filtrated. Then, the solid residues were carefully washed with dichloromethane. Dichloromethane and 1,2-dichlorobenzene were evaporated from the combined filtration solution. After which, methanol (100.0 ml) was added to a dark brown solid. After stirring for 30 minutes, a yellow solid product was collected by filtration. The pure product was obtained in the amount of 6.4 g (81.4%) by recrystallization from acetone/methanol.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtrated
  3. washThen, the solid residues were carefully washed with dichloromethane
  4. customDichloromethane and 1,2-dichlorobenzene were evaporated from the combined filtration solution
  5. additionAfter which, methanol (100.0 ml) was added to a dark brown solid
  6. stirringAfter stirring for 30 minutes
  7. filtrationa yellow solid product was collected by filtration
  8. customThe pure product was obtained in the amount of 6.4 g (81.4%) by recrystallization from acetone/methanol

Sources & evidence

ORD record
ord-9550969b36844ec8bd93b0d4c56875d9
Source dataset
uspto-grants-2013_10
Patent number
US08546505B2

Reaction notes

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