Tetrahydrofuran → HCID 10498284, compound

HRID 724934Notes

Reaction equation

HRID 724934 reaction equation
Cl[C:2]1[C:7]([NH:8][C:9]([C:11]2[C:12]([NH:18][CH2:19][CH3:20])=[N:13][CH:14]=[C:15]([Br:17])[CH:16]=2)=[O:10])=[CH:6][CH:5]=[C:4]([Cl:21])[N:3]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].O1CCCC1>N1C=CC=CC=1>[Br:17][C:15]1[CH:14]=[N:13][C:12]2[N:18]([CH2:19][CH3:20])[C:2]3[N:3]=[C:4]([Cl:21])[CH:5]=[CH:6][C:7]=3[NH:8][C:9](=[O:10])[C:11]=2[CH:16]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724254Sodium bis(trimethylsilyl)amideHCID 10524413HCID 10524413, compound

Product 1

HCID 10498284HCID 10498284, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of N-(2,6-dichloro-3-pyridinyl)-5-bromo-2-ethylamino-3-pyridinecarboxamide (5.9 g, 15 mmol) in 30 mL of pyridine at 50° C. under argon was added by syringe a 1.0M solution of sodium hexamethyldisilazide in tetrahydrofuran (31.5 mL, 31.5 mmol). After 10 min, the reaction mixture was diluted with ice water and allowed to stir for 2 hours. The resultant orange-yellow precipitate was collected by suction filtration and air-dried to give 4.9 g of the title compound.

Workup

  1. filtrationThe resultant orange-yellow precipitate was collected by suction filtration
  2. customair-dried

Sources & evidence

ORD record
ord-b896b2c7afd7457e9ae6f78ed352c23a
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

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