Isopropyl iodide → Ethyl 5-iodo-6-isopropoxynicotinate

HRID 1820981Notes

Reaction equation

HRID 1820981 reaction equation
[OH:1][C:2]1[C:12]([I:13])=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=1.I[CH:15]([CH3:17])[CH3:16].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[I:13][C:12]1[C:2]([O:1][CH:15]([CH3:17])[CH3:16])=[N:3][CH:4]=[C:5]([CH:11]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 178469850Ethyl 6-hydroxy-5-iodonicotinate

Product 1

HCID 68851282Ethyl 5-iodo-6-isopropoxynicotinateYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 500 mg (1.71 mmol) of ethyl 6-hydroxy-5-iodonicotinate (from Step A) in 10 mL of DMF were added 330 mg (1.96 mmol) of 2-iodopropane and 1.67 g (5.11 mmol) of cesium carbonate. After stirring at 50° C. for 16 h, the reaction mixture was partitioned between EtOAc (20 mL) and water (20 mL). The organic layer was washed with brine (3×20 mL), dried over MgSO4, and concentrated. Chromatography on a Biotage 25+M cartridge using 4:1 v/v hexanes/EtOAc as the eluant to afford 210 mg (37%) of a white solid as the title compound: 1H NMR (500 MHz, CDCl3) δ 1.40 (m, 9H), 4.37 (q, J=7.1, 2H), 5.37 (m, 1H), 8.59 (d, J=2.1, 1H), 8.74 (d, J=2.0, 1H).

Workup

  1. customthe reaction mixture was partitioned between EtOAc (20 mL) and water (20 mL)
  2. washThe organic layer was washed with brine (3×20 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-63def91415b842adb1ee0cc24b9d9d86
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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