2-Bromoethyl methyl ether → HCID 67123818, compound

HRID 1887019Notes

Reaction equation

HRID 1887019 reaction equation
[O:1]=[C:2]1[NH:10][C:9]2[C:4](=[N:5][C:6]([C:11]3[CH:12]=[N:13][N:14]4[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][C:15]=34)=[N:7][CH:8]=2)[N:3]1[CH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.[CH3:28][O:29][CH2:30][CH2:31]Br>CN(C=O)C.[H-].[Na+]>[CH3:28][O:29][CH2:30][CH2:31][N:10]1[C:9]2[C:4](=[N:5][C:6]([C:11]3[CH:12]=[N:13][N:14]4[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][C:15]=34)=[N:7][CH:8]=2)[N:3]([CH:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[C:2]1=[O:1]

Participants

5

Reactant 2

HCID 809722-Bromoethyl methyl etherHCID 52933409HCID 52933409, compound

Product 1

HCID 67123818HCID 67123818, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 24758Sodium hydrideSolvent

Procedure

To a solution of example 1 (50 mg, 0.14 mmol) in DMF (8 mL), 55-65% NaH dispersion in mineral oil (6 mg, 0.15 mmol) was added and the resulting solution was stirred at room temperature for 10 min. Then 2-bromoethyl methyl ether (0.032 mL, 0.34 mmol) was added and the reaction mixture was stirred at 50° C. for 14.5 h. The reaction mixture was quenched with H2O (10 mL) and extracted with EtOAc (3×10 mL). The combined organic phases were dried over anhydrous Na2SO4, filtered and concentrated. The crude product thus obtained was chromatographed over silica gel using EtOAc/hexanes mixtures of increasing polarity as eluent, to afford 36 mg of the desired compound (62% yield).

Workup

  1. stirringthe reaction mixture was stirred at 50° C. for 14.5 h
  2. customThe reaction mixture was quenched with H2O (10 mL)
  3. extractionextracted with EtOAc (3×10 mL)
  4. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product thus obtained
  8. customwas chromatographed over silica gel
  9. temperatureof increasing polarity as eluent

Sources & evidence

ORD record
ord-8fd20e2b5f384d5b998bbbabba878fce
Source dataset
uspto-grants-2013_08
Patent number
US08501735B2

Reaction notes

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