Sodium hydride → HCID 15614949, compound

HRID 620365Notes

Reaction equation

HRID 620365 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:18][CH3:19])[C:10]=2[C:14]([F:17])([F:16])[F:15])[C:5]=1[C:20]([NH:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:21].Br[CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31]>O1CCCC1>[Br:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:18][CH3:19])[C:10]=2[C:14]([F:17])([F:16])[F:15])[C:5]=1[C:20]([N:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[O:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 15614938HCID 15614938, compound

Product 1

HCID 15614949HCID 15614949, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

Sodium hydride (80% by weight dispersion in mineral oil, 0.347 g, 1.1 eq) was added to a stirred solution of 2-bromo-N-(ethoxycarbonyl)-6-methoxy-5-(trifluoromethyl)-1-naphthalenecarboxamide (4.41 g, 10.5 mmol) in anhydrous tetrahydrofuran (150 mL) at room temperture under a dry nitrogen atmosphere. After 1 hour, the t-butyl bromoacetate (2.54 mL, 1.5 eq) was added and the reaction was heated to 55° C. After 11/2 hours of heating, the reaction was cooled to room temperature and the THF was removed. The residue was suspended in ether (250 mL), washed with water (2×100 mL) and saturated aqueous NaCl (1×50 mL), dried with magnesium sulfate, and the ether was removed. The resultant oil was triturated with petroleum ether (1×50 mL) to provide the title compound as a white powder (4.78 g, 85%). A small samle was recrystallized in ether-petroleum ether to provide white crystals for analysis, m.p. 109.5°-112° C.

Workup

  1. temperatureAfter 11/2 hours of heating
  2. temperaturethe reaction was cooled to room temperature
  3. customthe THF was removed
  4. washwashed with water (2×100 mL) and saturated aqueous NaCl (1×50 mL)
  5. dry with materialdried with magnesium sulfate
  6. customthe ether was removed
  7. customThe resultant oil was triturated with petroleum ether (1×50 mL)

Sources & evidence

ORD record
ord-7fab2f6ce1a648838fdb1e2a2a440233
Source dataset
uspto-grants-1989_04
Patent number
US04820727

Reaction notes

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