Bromocyclopentane → HCID 22145703, compound

HRID 1994342Notes

Reaction equation

HRID 1994342 reaction equation
[CH:1]1(Br)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:7][C:8]1[C:9]([CH3:18])=[N:10][CH:11]=[C:12]([CH:17]=1)[C:13]([O:15][CH3:16])=[S:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:1]1([O:7][C:8]2[C:9]([CH3:18])=[N:10][CH:11]=[C:12]([CH:17]=2)[C:13]([O:15][CH3:16])=[S:14])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 22145740HCID 22145740, compound

Product 1

HCID 22145703HCID 22145703, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Cyclopentyl bromide (0.78 mL) is added to a stirred mixture of methyl 5-hydroxy-6-methylthionicotinoate (810 mg) and anhydrous potassium carbonate (1.8 g) in dry dimethylformamide (15 mL). The mixture is heated at 60±5° C. for 8 hours. After cooling the mixture is concentrated in vacuo and the residue partitioned between water and ethyl acetate. The ethyl acetate phase is isolated, washed with water and dried (MgSO4). The solvent is removed in vacuo to give methyl 5-cyclopentyloxy-6-methylthionicotinoate (920 mg) as a light brown oil. [Elemental analysis: —C, 58.41; H, 6.41; N, 5.24%. calculated: —C, 58.2; H, 6.44; N, 5.33%.].

Workup

  1. temperatureAfter cooling the mixture
  2. concentrationis concentrated in vacuo
  3. customthe residue partitioned between water and ethyl acetate
  4. customThe ethyl acetate phase is isolated
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-a69e6f25cec449ed88733800cf163935
Source dataset
uspto-grants-2010_01
Patent number
US07652144B2

Reaction notes

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