Cesium carbonate → HCID 24810335, compound

HRID 2081109Notes

Reaction equation

HRID 2081109 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:18][N:17]=[C:16]([CH3:19])[N:15]=2)=[CH:10][C:9]=1[OH:20].[CH2:21]([O:23][C:24]([C:26]1[C:27]2[S:35][CH:34]=[C:33]([CH2:36]Br)[C:28]=2[C:29]([Cl:32])=[N:30][CH:31]=1)=[O:25])[CH3:22]>O1CCCC1.CN(C)C=O>[CH2:21]([O:23][C:24]([C:26]1[C:27]2[S:35][CH:34]=[C:33]([CH2:36][O:20][C:9]3[CH:10]=[C:11]([C:14]4[O:18][N:17]=[C:16]([CH3:19])[N:15]=4)[CH:12]=[CH:13][C:8]=3[CH3:7])[C:28]=2[C:29]([Cl:32])=[N:30][CH:31]=1)=[O:25])[CH3:22]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 115300973-Bromomethyl-4-chloro-thieno[3,2-c]pyridine-7-carboxylic acid ethyl esterHCID 575815912-Methyl-5-(3-methyl-1,2,4-oxadiazol-5-yl)phenol

Product 1

HCID 24810335HCID 24810335, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of cesium carbonate (1.02 g, 3.13 mmol), 2-methyl-5-(3-methyl-[1,2,4]oxadiazol-5-yl)-phenol (0.42 g, 2.20 mmol) (from Example 52 supra) in tetrahydrofuran/N,N-dimethylformamide (5:2, 21 mL) was heated at 70° C. for 2 hours. 3-Bromomethyl-4-chloro-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (0.68 g, 2.04 mmol) (from Example 1 supra) was added. Heating was continued for 1 hour. The reaction mixture was partitioned between dichloromethane and water. The aqueous phase was extracted with dichloromethane (2×). The combined organic phase washed with water and brine, dried (magnesium sulfate) and concentrated. The residue was purified by flash chromatography eluting with 5-10% ethyl acetate in dichloromethane to give 4-chloro-3-[2-methyl-5-(3-methyl-[1,2,4]oxadiazol-5-yl)-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester. (Yield 0.51 g, 57%).

Workup

  1. temperatureHeating
  2. customThe reaction mixture was partitioned between dichloromethane and water
  3. extractionThe aqueous phase was extracted with dichloromethane (2×)
  4. washThe combined organic phase washed with water and brine
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography
  8. washeluting with 5-10% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-baf5ac6f8f8c47f9834efc321db51d82
Source dataset
uspto-grants-2011_04
Patent number
US07932390B2

Reaction notes

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