Water → HCID 78128152, compound

HRID 1483165Notes

Reaction equation

HRID 1483165 reaction equation
[C:1]([N-:5][CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][N:10]=1)[OH:8])(C)(C)C.[H-].[Na+].[OH2:18]>O1CCCC1>[Br:15][C:12]1[CH:13]=[CH:14][C:9]([CH:7]2[O:8][C:1](=[O:18])[NH:5][CH2:6]2)=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 131736720HCID 131736720, compound

Product 1

HCID 78128152HCID 78128152, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Compound 14a (70 mg, 0.85 mmol) was dissolved in dried tetrahydrofuran (5 mL), cooled to 0° C. NaH (51 mg, 1.28 mmol) was added, and after its completion, the reaction mixture was raised to room temperature, and then raised to 50° C. to react for 4 hrs. The reaction was monitored by TLC (petroleum ether/ethyl acetate=8/1). After the reaction completed, water was added, and the mixture was extracted with ethyl acetate. The organic phase was combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate. Column chromatography (petroleum ether/ethyl acetate=5/1) afforded 150 mg of white solid (compound 14b), yield 72%.

Workup

  1. temperatureafter its completion, the reaction mixture was raised to room temperature
  2. temperatureraised to 50° C.
  3. customto react for 4 hrs
  4. extractionthe mixture was extracted with ethyl acetate
  5. washwashed with saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-21470a7d23354deb94c0884fa4146e7b
Source dataset
uspto-grants-2016_08
Patent number
US09416144B2

Reaction notes

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