Methyl iodide → HCID 44447708, compound

HRID 1866853Notes

Reaction equation

HRID 1866853 reaction equation
[C:1]1([C:7]2([C:14]3[CH:19]=[C:18]([O:20][CH2:21][C:22]4[CH:31]=[CH:30][C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[N:23]=4)[CH:17]=[CH:16][C:15]=3[OH:32])[CH2:12][CH:11]3[CH2:13][CH:8]2[CH2:9][CH2:10]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:33](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C=O)C.O>[CH3:33][O:32][C:15]1[CH:16]=[CH:17][C:18]([O:20][CH2:21][C:22]2[CH:31]=[CH:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=2)=[CH:19][C:14]=1[C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:12][CH:11]2[CH2:13][CH:8]1[CH2:9][CH2:10]2

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 444477012-(2-Phenylbicyclo[2.2.1]heptan-2-yl)-4-(quinolin-2-ylmethoxy)phenol

Product 1

HCID 44447708HCID 44447708, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1b (200 mg, 0.47 mmol) in DMF (4 mL) was added cesium carbonate (186 mg, 0.57 mmol) followed by methyl iodide (35.0 μL, 0.57 mmol). The mixture was stirred at room temperature for 18 h, diluted with water (20 mL) and extracted three times with EtOAc. The combined organic extracts were washed three times with water, dried (MgSO4) and concentrated. The residue (210 mg) was triturated with a 1:1 mixture of hexane/ether to provide 1c as a solid (113 mg), m.p. 138-139° C.

Workup

  1. extractionextracted three times with EtOAc
  2. washThe combined organic extracts were washed three times with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue (210 mg) was triturated with a 1:1 mixture of hexane/ether

Sources & evidence

ORD record
ord-30421b9dc86a46fa85386d9d8b717db3
Source dataset
uspto-grants-2009_12
Patent number
US07629467B2

Reaction notes

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