Trimethylsilyldiazomethane → Methyl 1H-pyrrolo[2,3-b]pyridine-6-carboxylate

HRID 1527243Notes

Reaction equation

HRID 1527243 reaction equation
[NH:1]1[C:5]2=[N:6][C:7]([C:10]([OH:12])=[O:11])=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[CH3:13][Si](C=[N+]=[N-])(C)C>CO.CCOCC>[NH:1]1[C:5]2=[N:6][C:7]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 247288891H-Pyrrolo[2,3-b]pyridine-6-carboxylic acid

Product 1

HCID 57475482Methyl 1H-pyrrolo[2,3-b]pyridine-6-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 1H-pyrrolo[2,3-b]pyridine-6-carboxylic acid [898746-35-5] (500 mg, 3.08 mmol) in MeOH was added a 2M solution of trimethylsilyldiazomethane in Et2O at 0° C., and the reaction mixture was stirred at RT for 30 min. The reaction mixture was concentrated in vacuo to give the title compound. MS (LC/MS): 177 [M+H]+, 375 [2M+H]+; tR (HPLC conditions k): 2.71

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-375b280f0d9e4e2cb3b6e845daeb0bf3
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

Loading…