Potassium tert-butoxide → HCID 90093877, compound

HRID 1753073Notes

Reaction equation

HRID 1753073 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH:4]([N:6]1[C:14]2[C:13]([F:15])=[CH:12][N:11]=[CH:10][C:9]=2[C:8]([I:16])=[CH:7]1)[CH3:5].[CH3:18]C(C)([O-])C.[K+]>C1COCC1>[CH3:1][O:2][C:3](=[O:17])[C:4]([N:6]1[C:14]2[C:13]([F:15])=[CH:12][N:11]=[CH:10][C:9]=2[C:8]([I:16])=[CH:7]1)([CH3:18])[CH3:5]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 90093829HCID 90093829, compound

Product 1

HCID 90093877HCID 90093877, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-(7-fluoro-3-iodo-pyrrolo[3,2-c]pyridin-1-yl)-propionic acid methyl ester (8 g, 22.98 mmol) in dry THF (80 mL) was added Mel (1.85 mL, 29.87 mmol) and the flask was placed in a water bath. Potassium tert-butoxide (1M in THF, 29.87 mL, 29.87 mmol) was added over 10 minutes and the mixture was stirred for an additional 10 minutes. Then reaction was quenched with water and few drops of 0.2M HCl and then diluted with EtOAc. The organic layer was washed with water, brine, dried over sodium sulphate and evaporated in vacuo. The crude material was purified by silica gel column chromatography eluting with 0-20% EtOAc in Hexane to afford the title compound as light yellow solid (78%, 6.5 g).

Workup

  1. customthe flask was placed in a water bath
  2. customThen reaction
  3. customwas quenched with water and few drops of 0.2M HCl
  4. additiondiluted with EtOAc
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over sodium sulphate
  7. customevaporated in vacuo
  8. customThe crude material was purified by silica gel column chromatography
  9. washeluting with 0-20% EtOAc in Hexane

Sources & evidence

ORD record
ord-f9ced9c313524f8589b1c4728084a1fc
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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