Dimethylformamide → 1-(6-Chloro-benzo[b]thiophen-2-ylmethyl)-5-(2-methoxy-ethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:19][C:9]2=[CH:10][N:11]=[C:12]([O:14][CH2:15][CH2:16][O:17][CH3:18])[CH:13]=[C:8]2[CH:7]=1)=[O:5])[CH3:2].CN(C=O)C.Br[CH2:26][C:27]1[S:31][C:30]2[CH:32]=[C:33]([Cl:36])[CH:34]=[CH:35][C:29]=2[CH:28]=1>>[CH2:1]([O:3][C:4]([C:6]1[N:19]([CH2:26][C:27]2[S:31][C:30]3[CH:32]=[C:33]([Cl:36])[CH:34]=[CH:35][C:29]=3[CH:28]=2)[C:9]2=[CH:10][N:11]=[C:12]([O:14][CH2:15][CH2:16][O:17][CH3:18])[CH:13]=[C:8]2[CH:7]=1)=[O:5])[CH3:2]Participants
Procedure
To a solution of 660 mg (2.497 mmol) 5-(2-Methoxy-ethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid ethyl ester in 15 mL absolute DMF 24 mg (2.497 mmol) NaH (96%) were added in an argon atmosphere. The mixture was stirred for 30 min. at room temperature. 623 mg (2.497 mmol) 2-Bromomethyl-6-chloro-benzo[b]thiophene [prepared by adopting a procedure described by Ewing, William R. et al. in; PCT Int. Appl. (1999), 300 pp. WO 9937304 A1; and Ewing, William R. et al. PCT Int. Appl. (2001), 460 pp. WO 0107436 A2] were added and the mixture stirred for 1 h at room temperature. The solvent was removed in vacuo and the residue purified by preparative HPLC (eluent: CH3CN/H2O/0.1% CF3COOH). The fractions containing the product were combined, concentrated in vacuo and lyophilized. Yield: 900 mg.
Workup
- stirringthe mixture stirred for 1 h at room temperature
- customThe solvent was removed in vacuo
- customthe residue purified by preparative HPLC (eluent: CH3CN/H2O/0.1% CF3COOH)
- additionThe fractions containing the product
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-e23840ba8ca344138a642bd8f3ba66fb
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07317027B2
Reaction notes
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