Isopropyl iodide → N-{3-[4-(5-Isopropoxypyridin-2-yloxy)phenyl]-1-methylpropyl}acetamide

HRID 1260514Notes

Reaction equation

HRID 1260514 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH:17]([NH:19][C:20](=[O:22])[CH3:21])[CH3:18])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.I[CH:24]([CH3:26])[CH3:25].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH:24]([O:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH:17]([NH:19][C:20](=[O:22])[CH3:21])[CH3:18])=[CH:11][CH:10]=2)=[N:6][CH:7]=1)([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 67302795N-{3-[4-(5-Hydroxypyridin-2-yloxy)phenyl]-1-methylpropyl}acetamide

Product 1

HCID 44608623N-{3-[4-(5-Isopropoxypyridin-2-yloxy)phenyl]-1-methylpropyl}acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-{3-[4-(5-Hydroxypyridin-2-yloxy)phenyl]-1-methylpropyl}acetamide (50 mg, 166 μmol), 2-iodopropane (28 mg, 166 μmol) and cesium carbonate (135 mg, 416 μmol) were stirred in 3 ml of DMF at 50° C. for 3 h. The reaction mixture was concentrated in vacuo, and the residue was purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 35 mg (61%), M+H+: 343.16.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-e40de53d719e48009758d25f418e7183
Source dataset
uspto-grants-2013_06
Patent number
US08470841B2

Reaction notes

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