Sodium hydride → HCID 10256405, compound

HRID 1293486Notes

Reaction equation

HRID 1293486 reaction equation
[N+](C1C=CC([C:10]2[CH:22]=[C:21]([C:23]([O-])=[O:24])[C:20]3[C:19]4[C:14](=[C:15]([Cl:26])[CH:16]=[CH:17][CH:18]=4)[N:13]([CH2:27][C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[C:12]=3[C:11]=2[O:35][CH3:36])=CC=1)([O-])=O.[Cl:37][C:38]1[CH:39]=[N:40][CH:41]=[C:42]([Cl:45])[C:43]=1[NH2:44].[H-].[Na+]>CN(C=O)C>[Cl:37][C:38]1[CH:39]=[N:40][CH:41]=[C:42]([Cl:45])[C:43]=1[NH:44][C:23]([C:21]1[C:20]2[C:19]3[C:14](=[C:15]([Cl:26])[CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[C:12]=2[C:11]([O:35][CH3:36])=[CH:10][CH:22]=1)=[O:24]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 898884-Amino-3,5-dichloropyridineHCID 69280074HCID 69280074, compound

Product 1

HCID 10256405HCID 10256405, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-nitrophenyl-8-chloro-9-(4-Fluorobenzyl)-1-methoxy-9H-4-carbazole carboxylate (100 mg, 0.1982 mmoles) and 3,5-dichloro 4-amino pyridine (32.3 mg, 0.1982 mmoles) in dry DMF (7 mL), at 25° C. under nitrogen atmosphere, sodium hydride 55% (10.3 mg, 0.2576 mmoles) was added and stirred for 1 hr. The reaction mixtre 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 70 mg of the title compound.

Workup

  1. customThe reaction mixtre 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-64e97f453a414886ad3b32506d4768f0
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

Loading…