Methyl iodide → 5-(6-chloro-1-methyl-1H-pyrrolo[3,2-c]pyridin-2-yl)-nicotinic acid methyl ester

HRID 391318Notes

Reaction equation

HRID 391318 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([C:10]#[C:11][C:12]2[CH:13]=[N:14][C:15]([Cl:19])=[CH:16][C:17]=2[NH2:18])[CH:7]=[N:6][CH:5]=1.[CH3:21]C([O-])(C)C.[K+].CI>CN1C(=O)CCC1>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([C:10]2[N:18]([CH3:21])[C:17]3[CH:16]=[C:15]([Cl:19])[N:14]=[CH:13][C:12]=3[CH:11]=2)[CH:7]=[N:6][CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 59578429HCID 59578429, compound

Product 1

HCID 595784345-(6-chloro-1-methyl-1H-pyrrolo[3,2-c]pyridin-2-yl)-nicotinic acid methyl ester

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To 5-(4-amino-6-chloro-pyridin-3-ylethynyl)-nicotinic acid methyl ester (0.950 mg, 3.30 μmol) in NMP (15 mL) was added KOtBu (1.112 mg, 9.91 μmol) and the reaction was left to stir overnight at room temperature. The reaction was cooled to 0° C. and methyl iodide (0.619 μl, 9.91 μmol) was added. The reaction mixture was stirred for 30 min. The reaction was quenched with water and extracted with ethyl acetate twice. The combined organic layer was washed with water thrice, dried over sodium sulfate and concentrated in vacuo to afford desired product 5-(6-chloro-1-methyl-1H-pyrrolo[3,2-c]pyridin-2-yl)-nicotinic acid methyl ester as a brown color oil which was taken onto next step without further purification. ESI-MS: m/z 302.0 (M+H)+

Workup

  1. waitthe reaction was left
  2. temperatureThe reaction was cooled to 0° C.
  3. stirringThe reaction mixture was stirred for 30 min
  4. customThe reaction was quenched with water
  5. extractionextracted with ethyl acetate twice
  6. washThe combined organic layer was washed with water thrice
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c2803d5012b642c08fe3457d58bd6892
Source dataset
uspto-grants-2013_02
Patent number
US08383827B2

Reaction notes

Loading…