Cesium carbonate → HCID 24810140, compound

HRID 2081085Notes

Reaction equation

HRID 2081085 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][O:8][C:9]1[CH:27]=[CH:26][C:12]([CH2:13][N:14]2[N:18]=[N:17][C:16]([C:19]3[CH:20]=[C:21]([OH:25])[CH:22]=[CH:23][CH:24]=3)=[N:15]2)=[CH:11][CH:10]=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:25][C:21]3[CH:22]=[CH:23][CH:24]=[C:19]([C:16]4[N:17]=[N:18][N:14]([CH2:13][C:12]5[CH:11]=[CH:10][C:9]([O:8][CH3:7])=[CH:27][CH:26]=5)[N:15]=4)[CH:20]=3)[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 59649708HCID 59649708, compound

Product 1

HCID 24810140HCID 24810140, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of cesium carbonate (0.60 g, 1.83 mmol), 3-[2-(4-methoxy-benzyl)-2H-tetrazol-5-yl]-phenol (0.38 g, 1.35 mmol) (from Example 26 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 (0.41 g, 1.22 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 hexanes to give 4-chloro-3-{3-[2-(4-methoxy-benzyl)-2H-tetrazol-5-yl]-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 (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography
  8. washeluting with 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-65baec6eced84d4eb15b713a8ae5912c
Source dataset
uspto-grants-2011_04
Patent number
US07932390B2

Reaction notes

Loading…