Potassium Iodide → HCID 59649707, compound

HRID 2081068Notes

Reaction equation

HRID 2081068 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=2)=[N:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.[CH2:38]([O:40][C:41]([C:43]1[C:44]2[S:52][CH:51]=[C:50]([CH2:53]Br)[C:45]=2[C:46]([Cl:49])=[N:47][CH:48]=1)=[O:42])[CH3:39].[I-].[K+]>CN(C)C=O>[CH2:38]([O:40][C:41]([C:43]1[C:44]2[S:52][CH:51]=[C:50]([CH2:53][O:13][C:9]3[CH:10]=[CH:11][CH:12]=[C:7]([C:5]4[O:6][C:2]([CH3:1])=[N:3][N:4]=4)[CH:8]=3)[C:45]=2[C:46]([Cl:49])=[N:47][CH:48]=1)=[O:42])[CH3:39]

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 115300973-Bromomethyl-4-chloro-thieno[3,2-c]pyridine-7-carboxylic acid ethyl esterHCID 129617433-(5-Methyl-1,3,4-oxadiazol-2-yl)phenol

Product 1

HCID 59649707HCID 59649707, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A suspension of 3-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenol (0.15 g, 0.85 mmol) (from Example 7 supra), potassium carbonate (0.25 g, 1.8 mmol) and 18-Crown-6 (10 mg, 0.04 mmol) (Aldrich) in N,N-dimethylformamide (5 mL) was heated at 65° C. in a sealed tube with magnetic stirring for 2 hours. 3-Bromomethyl-4-chloro-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (0.27 g, 0.8 mmol) (from Example 1 supra) and potassium iodide (0.13 g, 0.8 mmol) were then added and mixture heated at 65° C. in the sealed tube for another 20 hours. After cooling, mixture was partitioned between ethyl acetate (2×100 mL) and water (2×100 mL). Organic layers were washed with brine, then combined, dried (MgSO4), filtered and concentrated. Residue was purified by flash chromatography (Biotage 40S, 20% ethyl acetate in dichloromethane as solvent) to give 4-chloro-3-[3-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester as a white powder. (Yield 0.22 g, 63.1%).

Workup

  1. temperaturemixture heated at 65° C. in the sealed tube for another 20 hours
  2. temperatureAfter cooling
  3. custommixture was partitioned between ethyl acetate (2×100 mL) and water (2×100 mL)
  4. washOrganic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customResidue was purified by flash chromatography (Biotage 40S, 20% ethyl acetate in dichloromethane as solvent)

Sources & evidence

ORD record
ord-2d223fef52cf41b0bacc07f6ec590102
Source dataset
uspto-grants-2011_04
Patent number
US07932390B2

Reaction notes

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