1,8-Diazabicyclo(5.4.0)undec-7-ene → Methyl benzothieno[3,2-c]pyridine-3-carboxylate

HRID 1073008Notes

Reaction equation

HRID 1073008 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH:10]=O)=[C:2]1[CH:12]=O.C([NH:17][CH:18](P(OC)(OC)=O)[C:19]([O:21][CH3:22])=[O:20])(=O)C.N12CCCN=C1CCCCC2>C(Cl)Cl>[CH:10]1[C:3]2[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[S:1][C:2]=2[CH:12]=[C:18]([C:19]([O:21][CH3:22])=[O:20])[N:17]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11746707Methyl 2-acetamido-2-(dimethoxyphosphoryl)acetateHCID 12202920Benzo[b]thiophene-2,3-dicarboxaldehyde2×

Product 1

HCID 22047428Methyl benzothieno[3,2-c]pyridine-3-carboxylateYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-Benzothiophene-2,3-dicarbaldehyde (C180) (1.91 g, 10.0 mmol) is dissolved in CH2Cl2 (100 ml) and chilled in an ice bath. Methyl (acetylamino)(dimethoxyphosphoryl)acetate (C152) (2.63 g, 11.0 mmol) is dissolved in CH2Cl2 (50 ml) and added to 1,8-diazabicyclo[5.4.0]undec-7-ene (1.65 ml, 11.0 mmol), stirring for 5 minutes. This solution is added dropwise to the chilled thiophene solution. The reaction mixture is stirred in the ice bath for 1 h and then over night at rt. The reaction is concentrated in vacuo and the crude material is chromatographed over 500 g slurry-packed silica eluting with 50% ethyl acetate/hexane to afford methyl benzothieno[3,2-c]pyridine-3-carboxylate (C 181) as a white solid (73% yield). MS for C13H9NO2S, (EI) m/z: 243 (M)+.

Workup

  1. temperaturechilled in an ice bath
  2. waitover night at rt
  3. concentrationThe reaction is concentrated in vacuo
  4. customthe crude material is chromatographed over 500 g slurry-packed silica eluting with 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-1fc7e64f7f8446f28eee6f78511945a1
Source dataset
uspto-grants-2005_06
Patent number
US06911543B2

Reaction notes

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