1-Bromo-2-methylpropane → HCID 178490655, compound

HRID 254672Notes

Reaction equation

HRID 254672 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[S:11][C:12]2[C:18]([CH3:20])([CH3:19])[O:17][CH2:16][CH2:15][C:13]=2[N:14]=1)=[O:8].[CH3:24][C:25]([CH3:28])([O-])[CH3:26].[K+].BrCC(C)C>CN(C=O)C.C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([CH:21]=1)[C:7](/[N:9]=[C:10]1\[S:11][C:12]2[C:18]([CH3:19])([CH3:20])[O:17][CH2:16][CH2:15][C:13]=2[N:14]\1[CH2:24][CH:25]([CH3:28])[CH3:26])=[O:8]

Participants

6

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 23665647Potassium tert-butoxideHCID 871795845-Chloro-n-(4,4-dimethyl-6,7-dihydro-4h-pyrano[4,3-d]thiazol-2-yl)-2-methoxybenzamide

Product 1

HCID 178490655HCID 178490655, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of Example 89F (1.0 g, 2.8 mmol) in DMF/THF (1:4, 20 mL) were added potassium tert-butoxide (0.35 g, 3.1 mmol, Aldrich), 1-bromo-2-methylpropane (0.43 g, 3.1 mmol, Aldrich) and tetrabutylammonium iodide (0.1 g, 0.3 mmol, Aldrich). The reaction mixture was stirred at 80° C. for 16 h, cooled to room temperature, quenched with saturated aqueous NaHCO3 (20 mL). The aqueous layer was extracted with ethyl acetate (3×20 mL). The combined organic extracts were dried over anhydrous (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash280 ™ (SiO2, 0-1% methanol in dichloromethane) to afford 90 mg (29%) of the title compound. MS (ESI+) m/z 409 (M+H)+

Workup

  1. temperaturecooled to room temperature
  2. customquenched with saturated aqueous NaHCO3 (20 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×20 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-3f08a5ac57304e3aa1b12dad22683118
Source dataset
uspto-grants-2011_01
Patent number
US07875640B2

Reaction notes

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