Tetrahydrofuran → 8-Bromo-11-ethyl-5,11-dihydro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 2229303Notes

Reaction equation

HRID 2229303 reaction equation
Cl[C:2]1[C:7]([C:8]([NH:10][C:11]2[C:12]([NH:17][CH2:18][CH3:19])=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:9])=[CH:6][C:5]([Br:20])=[CH:4][N:3]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].C1COCC1>N1C=CC=CC=1>[Br:20][C:5]1[CH:4]=[N:3][C:2]2[N:17]([CH2:18][CH3:19])[C:12]3[N:13]=[CH:14][CH:15]=[CH:16][C:11]=3[NH:10][C:8](=[O:9])[C:7]=2[CH:6]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724254Sodium bis(trimethylsilyl)amideHCID 120157285-Bromo-2-chloro-N-[2-(ethylamino)pyridin-3-yl]pyridine-3-carboxamide

Product 1

HCID 120157298-Bromo-11-ethyl-5,11-dihydro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-oneYield 75%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-chloro-N-{2-(ethylamino)-3-pyridinyl}-5-bromo-3-pyridinecarboxamide (54.9 g, 154.4 mmol) in pyridine (308 mL) at 50° C. was added drop-wise a 1 M solution of NaHMDS (sodium hexamethyldisilazide) in THF (355 mL, 355 mmol). After 10 min, the reaction was allowed to cool to room temperature, and then was poured over ice water (2 L). The resulting solid was filtered, rinsed with water and then hexane. The solid was dried under reduced pressure to give the title compound (36 g, 75% yield) as a dark green solid.

Workup

  1. filtrationThe resulting solid was filtered
  2. washrinsed with water
  3. customThe solid was dried under reduced pressure

Sources & evidence

ORD record
ord-1d89d4079a874fb8bebf53aab3de110b
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

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