Sodium Methoxide → HCID 59783561, compound

HRID 718048Notes

Reaction equation

HRID 718048 reaction equation
Cl[C:2]1[C:7]([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])=[CH:6][CH:5]=[C:4]([C:18]([F:21])([F:20])[F:19])[N:3]=1.C[O-].[Na+]>O>[F:19][C:18]([F:21])([F:20])[C:4]1[CH:5]=[CH:6][C:7]2[NH:8][C:9](=[O:17])[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[O:16][C:2]=2[N:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 59783845HCID 59783845, compound

Product 1

HCID 59783561HCID 59783561, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
220 °C

Procedure

To a stirring solution of title compound 73 (0.76 g, 2.4 mmol) in tetraglyne (10 mL) was added sodium methoxide (0.220 g, 4.08 mmol) and the reaction mixture was stirred at 220° C. for 3 h. The reaction mixture was cooled to room temperature diluted with water (25 mL), stirred for 20 min then filtered to give a light brown solid which was purified by flash chromatography (0% to 60% ethyl acetate in hexanes) to afford title compound 74 (0.37 g, 55%). LRMS (ESI): (calc) 280.05. (found) 281.3 (MH)+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringstirred for 20 min
  3. filtrationthen filtered
  4. customto give a light brown solid which
  5. customwas purified by flash chromatography (0% to 60% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-544431c3ce6e4ab28ca14887f024bfd9
Source dataset
uspto-grants-2015_11
Patent number
US09193749B2

Reaction notes

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