1-Bromo-3-methylbutane → HCID 67970930, compound

HRID 1470752Notes

Reaction equation

HRID 1470752 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[CH:21]=[CH:20][C:19]([C@@H:22]([NH:24][C:25](=[O:27])[CH3:26])[CH3:23])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1.Br[CH2:29][CH2:30][CH:31]([CH3:33])[CH3:32]>CN(C=O)C>[CH2:29]([O:3][C:4]1[CH:5]=[C:6]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[CH:17]=[CH:18][C:19]([C@@H:22]([NH:24][C:25](=[O:27])[CH3:26])[CH3:23])=[CH:20][CH:21]=3)[CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1)[CH2:30][CH:31]([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 78911-Bromo-3-methylbutaneHCID 24758Sodium hydrideHCID 67125421HCID 67125421, compound2×

Product 1

HCID 67970930HCID 67970930, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

8 mg (0.2 mmol) NaH (60% in mineral oil) are added to a mixture of 34 mg (0.10 mmol) (S)—N-{1-(4-[1-(3-hydroxyphenyl)-piperidin-4-yl]-phenyl}-ethyl)-acetamide (compound 1.27) and 23 mg (0.15 mmol) 1-bromo-3-methylbutane in 2 mL DMF at 0° C. The mixture is stirred at 70° C. for 3 d. The reaction mixture is quenched with water, filtered and the solvent is evaporated. The residue is purified using reversed phase HPLC (water/MeOH, 0.1% TFA) to yield the desired product.

Workup

  1. customThe reaction mixture is quenched with water
  2. filtrationfiltered
  3. customthe solvent is evaporated
  4. customThe residue is purified

Sources & evidence

ORD record
ord-56726cb8116243949dae2f7e2184cf61
Source dataset
uspto-grants-2015_04
Patent number
US09006450B2

Reaction notes

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