Methyl iodide → methyl 2-(3-iodo-1H-pyrrolo[3,2-c]pyridin-1-yl)-2-methylpropanoate

HRID 1753070Notes

Reaction equation

HRID 1753070 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH:4]([N:6]1[C:14]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[C:8]([I:15])=[CH:7]1)[CH3:5].CI.[CH3:19]C(C)([O-])C.[K+]>C1COCC1>[I:15][C:8]1[C:9]2[CH:10]=[N:11][CH:12]=[CH:13][C:14]=2[N:6]([C:4]([CH3:19])([CH3:5])[C:3]([O:2][CH3:1])=[O:16])[CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 900938402-(3-Iodo-pyrrolo[3,2-c]pyridine-1-yl)-propionic acid methyl ester

Product 1

HCID 90094007methyl 2-(3-iodo-1H-pyrrolo[3,2-c]pyridin-1-yl)-2-methylpropanoateYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(3-iodo-pyrrolo[3,2-c]pyridine-1-yl)-propionic acid methyl ester (Preparation 57, 13.1 g, 39.7 mmol) in THF (15 mL) was added methyl iodide (2.96 mL, 47.6 mmol) followed immediately by a 1M solution of potassium tertbutoxide in THF (5.34 g, 47.6 mmol) and the reaction was stirred at room temperature for 15 minutes. The reaction was quenched with water, and the remaining THF removed in vacuo. The residue was extracted with EtOAc, dried and concentrated in vacuo to afford the title compound as a yellow solid (5.1 g, 37%).

Workup

  1. customThe reaction was quenched with water
  2. customthe remaining THF removed in vacuo
  3. extractionThe residue was extracted with EtOAc
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d2c0d9c1953e4cf0bdd65e51bb6f7ac6
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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