3,3-Dimethylbutanoyl chloride → HCID 59754780, compound

HRID 751446Notes

Reaction equation

HRID 751446 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[C:5]([CH3:27])([CH3:26])[CH2:6][C:7]1[N:15]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[C:14]2[C:9](=[N:10][C:11]([O:24][CH3:25])=[CH:12][CH:13]=2)[CH:8]=1)[CH3:2].[CH3:29][C:30]([CH3:36])([CH3:35])[CH2:31][C:32](Cl)=[O:33].[Cl-].[Al+3].[Cl-].[Cl-]>ClC(Cl)C>[CH2:1]([O:3][C:4](=[O:28])[C:5]([CH3:27])([CH3:26])[CH2:6][C:7]1[N:15]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)[C:14]2[C:9](=[N:10][C:11]([O:24][CH3:25])=[CH:12][CH:13]=2)[C:8]=1[C:32](=[O:33])[CH2:31][C:30]([CH3:36])([CH3:35])[CH3:29])[CH3:2]

Participants

5

Reactant 3

HCID 815143,3-Dimethylbutanoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 59754773HCID 59754773, compound

Product 1

HCID 59754780HCID 59754780, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

3-[5-Methoxy-1-(4-chloro-benzyl)-1H-pyrrolo[3,2-b]pyridin-2-yl]-2,2-dimethyl-propionic acid ethyl ester (Example 5, Step 4; 0.133 g, 0.33 mmol) was dissolved in dichloroethane (5 mL). 3,3-Dimethyl-butyryl chloride (0.12 mL, 0.86 mmol) and aluminum chloride (0.137 g, 1.03 mmol) were added, and the reaction was heated to 80° C. under N2 for 1.5 hours. The reaction mixture was cooled to room temperature and quenched with saturated potassium sodium tartrate tetrahydrate solution. The mixture was extracted with EtOAc three times, the combined organic layers were washed with water and brine, dried over MgSO4, filtered, and concentrated. The crude material was purified on silica gel (0-50% EtOAc in hexanes) to give the desired product.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customquenched with saturated potassium sodium tartrate tetrahydrate solution
  3. extractionThe mixture was extracted with EtOAc three times
  4. washthe combined organic layers were washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified on silica gel (0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-39a5bedfba674405a4fdfaaa9a0cae52
Source dataset
uspto-grants-2008_07
Patent number
US07405302B2

Reaction notes

Loading…