2-Bromopropane → HCID 69055747, compound

HRID 734859Notes

Reaction equation

HRID 734859 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH2:10][CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[C:6]([OH:8])[CH:7]=1.Br[CH:18]([CH3:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[I:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH2:10][CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[C:6]([O:8][CH:18]([CH3:20])[CH3:19])[CH:7]=1

Participants

6

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 69061413HCID 69061413, compound

Product 1

HCID 69055747HCID 69055747, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

A suspension of 0.15 g (0.45 mmol) of 5-iodo-2-(2-pyrrolidin-1-ylethoxy)phenol (Example 33.1c), 52 μL (0.55 mmol) of 2-bromopropane, and 186 mg (1.35 mmol) of potassium carbonate in 2 mL of acetonitrile was stirred for 2 hours at 75° C. The reaction mixture was diluted with water and the aqueous phase exhaustively extracted with DCM. The combined organic extracts were washed with saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, and evaporated down in vacuo. Yield: 77 mg (46% of theoretical); C15H22INO2 (M=375.245); calc.: molpeak (M+H)+: 376; found: molpeak (M+H)+: 376; HPLC-MS: 5.86 minutes (method A).

Workup

  1. extractionthe aqueous phase exhaustively extracted with DCM
  2. washThe combined organic extracts were washed with saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated down in vacuo
  5. custom5.86 minutes (method A)

Sources & evidence

ORD record
ord-5203a71d861048dabc6a3112e27b5c17
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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