Potassium Iodide → HCID 24810186, compound

HRID 2081089Notes

Reaction equation

HRID 2081089 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]2[S:15][CH:14]=[C:13]([CH2:16]Br)[C:8]=2[C:9]([Cl:12])=[N:10][CH:11]=1)=[O:5])[CH3:2].[CH3:18][N:19]1[N:23]=[N:22][C:21]([C:24]2[CH:25]=[C:26]([OH:30])[CH:27]=[CH:28][CH:29]=2)=[N:20]1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[S:15][CH:14]=[C:13]([CH2:16][O:30][C:26]3[CH:27]=[CH:28][CH:29]=[C:24]([C:21]4[N:22]=[N:23][N:19]([CH3:18])[N:20]=4)[CH:25]=3)[C:8]=2[C:9]([Cl:12])=[N:10][CH:11]=1)=[O:5])[CH3:2]

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 536765503-(2-methyl-2H-tetrazol-5-yl)-phenol

Product 1

HCID 24810186HCID 24810186, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 3-bromomethyl-4-chloro-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (042 g, 1.24 mmol) (from Example 1 supra), 3-(2-methyl-2H-tetrazol-5-yl)-phenol (0.23 g, 1.31 mmol) (from Example 30 supra), potassium iodide (0.21 g, 1.24 mmol), potassium carbonate (0.38 g, 2.78 mmol) and 18-crown-6 (16.0 mg, 0.06 mmol) in N,N-dimethylformamide (15 mL) was heated at 65° C. for 1 day. The reaction mixture was partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate (2×). The combined organic phase washed with water and brine, dried (MgSO4) and concentrated. The residue was purified by flash chromatography eluting with 30% ethyl acetate in hexanes to give 4-chloro-3-[3-(2-methyl-2H-tetrazol-5-yl)-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester. (Yield 0.15 g, 28%).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. extractionThe aqueous phase was extracted with ethyl acetate (2×)
  3. washThe combined organic phase washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. washeluting with 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-686cc38992494e73b633319f6106c776
Source dataset
uspto-grants-2011_04
Patent number
US07932390B2

Reaction notes

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