Cesium carbonate → HCID 24810137, compound

HRID 2081080Notes

Reaction equation

HRID 2081080 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]=[N:16][N:17]([CH3:19])[CH:18]=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[N:15]=[N:16][N:17]([CH3:19])[CH:18]=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 596497102-methyl-5-(1-methyl-1H-[1,2,3]triazol-4-yl)-phenol

Product 1

HCID 24810137HCID 24810137, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of cesium carbonate (0.56 g, 1.73 mmol) (Aldrich), 2-methyl-5-(1-methyl-1H-[1,2,3]triazol-4-yl)-phenol (0.24 g, 1.27 mmol) (from Example 21 supra) in tetrahydrofuran-N,N-dimethylformamide (5:2, 17.5 mL) was heated at 70° C. for 3 hours. 3-Bromomethyl-4-chloro-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (0.40 g, 1.15 mmol) (from Example 1 supra) was added. Heating was continued for 18 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 (MgSO4) and concentrated. The residue was purified by flash chromatography eluting with 30% ethyl acetate in dichloromethane to give 4-chloro-3-[2-methyl-5-(1-methyl-1H-[1,2,3]triazol-4-yl)-phenoxy-methyl]-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester. (Yield 0.25 g, 48%).

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 (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography
  8. washeluting with 30% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-a19d972dec2649108b9a87de5024a04d
Source dataset
uspto-grants-2011_04
Patent number
US07932390B2

Reaction notes

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