Methanol → 1-(6-Chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone

HRID 1527259Notes

Reaction equation

HRID 1527259 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].[C:15](Cl)(=[O:17])[CH3:16].CO>C(Cl)Cl>[Cl:1][C:2]1[N:10]=[C:9]2[NH:8][CH:7]=[C:6]([C:15](=[O:17])[CH3:16])[C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 113441186-Chloro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 717210681-(6-Chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Chloro-7-azaindole (1 g, 6.55 mmol) was added to a suspension of AlCl3 (4.37 g, 32.8 mmol) in CH2Cl2 (150 mL) under nitrogen atmosphere. The mixture was stirred at RT for 30 min, and acetyl chloride (2.34 mL, 32.8 mmol) was added dropwise. The resulting mixture was further stirred at RT for 2 h. After completion, MeOH (40 mL) was added cautiously and volatils were removed under reduced pressure. The residue was diluted in CH2Cl2 and neutralized by addition of a saturated aqueous solution of NaHCO3. The layers were separated and the organic extracts were dried (Na2SO4), filtered and concentrated. The crude residue was purified twice by flash column chromatography on silica gel (CH2Cl2 to CH2Cl2/MeOH 95-5). TLC, Rf (CH2Cl2/MeOH 9:1)=0.5; MS (UPLC/MS): 195.1/197.1 [M+H]+, 193.1/195.1 [M−H]−; tR (HPLC conditions f): 1.54 min.

Workup

  1. stirringThe resulting mixture was further stirred at RT for 2 h
  2. customvolatils were removed under reduced pressure
  3. additionThe residue was diluted in CH2Cl2
  4. additionneutralized by addition of a saturated aqueous solution of NaHCO3
  5. customThe layers were separated
  6. dry with materialthe organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude residue was purified twice by flash column chromatography on silica gel (CH2Cl2 to CH2Cl2/MeOH 95-5)
  10. custom1.54 min.

Sources & evidence

ORD record
ord-7b67bd4db21642e998343d46a944f074
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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