Tetrahydrofuran → HCID 18466606, compound

HRID 2229316Notes

Reaction equation

HRID 2229316 reaction equation
Cl[C:2]1[C:7]([C:8]([NH:10][C:11]2[C:12]([NH:18][CH2:19][CH3:20])=[N:13][C:14]([F:17])=[CH:15][CH:16]=2)=[O:9])=[CH:6][C:5]([Br:21])=[CH:4][N:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C1COCC1>N1C=CC=CC=1>[Br:21][C:5]1[CH:4]=[N:3][C:2]2[N:18]([CH2:19][CH3:20])[C:12]3[N:13]=[C:14]([F:17])[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 184666372-Chloro-N-{2-(ethylarnino)-6-fluoro-3pyridinyl}-5-bromo-3-pyridinecarboxamide

Product 1

HCID 18466606HCID 18466606, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of the 2-chloro-N-{2-(ethylamino)-6-fluoro-3-pyridinyl}-5-bromo-3-pyridinecarboxamide (73.5 g, 216 mmol) in pyridine (435 mL) at 50° C. was added drop-wise a 1 M solution of NaHMDS in THF (520 mL, 520 mmol). After 10 min, the reaction was allowed to cool to room temperature, then poured over ice water (2 L). The resulting solid was filtered, rinse with water and then hexane. The solid was dried under reduced pressure to give the title compound (50.6 g, 69% yield) as a dark green solid.

Workup

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

Sources & evidence

ORD record
ord-32cb6215182042ba8a6c3b4b434417fe
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

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