(2-Bromoethoxy)-tert-butyldimethylsilane → HCID 67124103, compound

HRID 1843125Notes

Reaction equation

HRID 1843125 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.Br[CH2:29][CH2:30][O:31][Si](C(C)(C)C)(C)C>CN(C=O)C.[H-].[Na+]>[OH:31][CH2:30][CH2:29][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 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 52933409HCID 52933409, compound

Product 1

HCID 67124103HCID 67124103, compoundYield 96.9%

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. The resulting solution was stirred at room temperature for 10 min. Then (2-bromoethoxy)-tert-butyldimethylsilane (0.074 mL, 0.34 mmol) was added and the reaction 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 hexanes/EtOAc mixtures of increasing polarity as eluent, to afford 55 mg of the desired compound (76% yield).

Workup

  1. stirringthe reaction 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-0170cd73991746c38f5e5bef0c4913d7
Source dataset
uspto-grants-2015_02
Patent number
US08946257B2

Reaction notes

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