Sodium hydride → HCID 10071621, compound

HRID 1293488Notes

Reaction equation

HRID 1293488 reaction equation
[N+](C1C=CC([C:10]2[CH:22]=[C:21]([C:23]([O-:25])=O)[C:20]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([Cl:26])[CH:18]=4)[N:13]([CH3:27])[C:12]=3[C:11]=2[O:28][CH3:29])=CC=1)([O-])=O.[Cl:30][C:31]1[CH:32]=[N:33][CH:34]=[C:35]([Cl:38])[C:36]=1[NH2:37].[H-].[Na+]>CN(C=O)C>[Cl:30][C:31]1[CH:32]=[N:33][CH:34]=[C:35]([Cl:38])[C:36]=1[NH:37][C:23]([C:21]1[C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([Cl:26])[CH:18]=3)[N:13]([CH3:27])[C:12]=2[C:11]([O:28][CH3:29])=[CH:10][CH:22]=1)=[O:25]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 898884-Amino-3,5-dichloropyridineHCID 69280111HCID 69280111, compound

Product 1

HCID 10071621HCID 10071621, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-nitrophenyl-6-chloro-1-methoxy-9-methyl-9H-4-carbazole carboxylate (160 mg, 0.4255 mmoles), and 3,5-dichloro-4-amino pyridine (69.36 mg, 0.4255 mmoles) in dry DMF (7 mL) at 25° C., sodium hydride 55% (34 mg, 0.8510 mmoles) was added and stirred under nitrogen atmosphere for 1 hr. The reaction mixture was quenched in ice cold water (25 mL) and extracted with ethyl acetate (2×25 mL). The organic layer was washed with bicarbonate (2×25 mL), followed by 1N HCl (2×25 mL) and with brine (25 mL), dried over sodium sulphate and concentrated to give the 90 mg of the title compound.

Workup

  1. customThe reaction mixture was quenched in ice cold water (25 mL)
  2. extractionextracted with ethyl acetate (2×25 mL)
  3. washThe organic layer was washed with bicarbonate (2×25 mL)
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3c60d1874b2c4f54845cf803e812e340
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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