Cesium carbonate → HCID 59649716, compound

HRID 2081099Notes

Reaction equation

HRID 2081099 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:7][C:8]1[CH:27]=[CH:26][C:11]([CH2:12][C:13]2[O:17][C:16]([C:18]3[CH:19]=[CH:20][C:21]([CH3:25])=[C:22]([OH:24])[CH:23]=3)=[N:15][N:14]=2)=[CH:10][CH:9]=1.[CH2:28]([O:30][C:31]([C:33]1[C:34]2[S:42][CH:41]=[C:40]([CH2:43]Br)[C:35]=2[C:36]([Cl:39])=[N:37][CH:38]=1)=[O:32])[CH3:29]>O1CCCC1.CN(C)C=O>[CH2:28]([O:30][C:31]([C:33]1[C:34]2[S:42][CH:41]=[C:40]([CH2:43][O:24][C:22]3[CH:23]=[C:18]([C:16]4[O:17][C:13]([CH2:12][C:11]5[CH:26]=[CH:27][C:8]([Cl:7])=[CH:9][CH:10]=5)=[N:14][N:15]=4)[CH:19]=[CH:20][C:21]=3[CH3:25])[C:35]=2[C:36]([Cl:39])=[N:37][CH:38]=1)=[O:32])[CH3:29]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 115300973-Bromomethyl-4-chloro-thieno[3,2-c]pyridine-7-carboxylic acid ethyl esterHCID 59649713HCID 59649713, compound

Product 1

HCID 59649716HCID 59649716, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
68 °C

Procedure

A suspension of cesium carbonate (0.54 g, 1.66 mmol), 5-[5-(4-chloro-benzyl)-[1,3,4]-oxadiazol-2-yl]-2-methyl-phenol (0.36 g, 1.20 mmol) (from Example 40 supra) in tetrahydrofuran/N,N-dimethylformamide (5:2, 21 mL) was heated at 68° C. for 2 hours. 3-Bromomethyl-4-chloro-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (0.36 g, 1.08 mmol) (from Example 1 supra) was added. Heating was continued for 2 hours. 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 (magnesium sulfate) and concentrated. The residue washed with ethyl acetate and dried to give 4-chloro-3-{5-[5-(4-chloro-benzyl)-[1,3,4]oxadiazol-2-yl]-2-methyl-phenoxymethyl}-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester. (Yield 0.17 g, 26%).

Workup

  1. temperatureHeating
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. extractionThe aqueous phase was extracted with ethyl acetate (2×)
  4. washThe combined organic phase washed with water and brine
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated
  7. washThe residue washed with ethyl acetate
  8. customdried

Sources & evidence

ORD record
ord-071ecacc4f9b450f80ab67f858a75c8c
Source dataset
uspto-grants-2011_04
Patent number
US07932390B2

Reaction notes

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