3-chloro-5-oxo-5H-benzo[4,5]cyclohepta[1,2-b]pyridine-7-carbaldehyde → 3-chloro-7-(1-hydroxypropyl)-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one

HRID 222303Notes

Reaction equation

HRID 222303 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[O:13])[C:11]3[CH:14]=[C:15]([CH:18]=[O:19])[CH:16]=[CH:17][C:10]=3[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1.[CH2:20]([Mg]Cl)[CH3:21]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[O:13])[C:11]3[CH:14]=[C:15]([CH:18]([OH:19])[CH2:20][CH3:21])[CH:16]=[CH:17][C:10]=3[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 577228923-chloro-5-oxo-5H-benzo[4,5]cyclohepta[1,2-b]pyridine-7-carbaldehydeHCID 178461633HCID 178461633, compound

Product 1

HCID 577229483-chloro-7-(1-hydroxypropyl)-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-chloro-5-oxo-5H-benzo[4,5]cyclohepta[1,2-b]pyridine-7-carbaldehyde (25 mg, 0.093 mmol) was dissolved in 4 mL of hot dichloromethane. The solution was cooled to room temperature and ethylmagnesium chloride (0.047 mL of 2.0 M in THF, 0.093 mmol) was added. The reaction was stirred at room temperature for 1.5 hours at which point it was quenched via the addition of saturated aqueous ammonium chloride. The mixture was extracted three times with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered, concentrated in vacuo, and purified via flash chromatography (silica, 5-60% ethyl acetate/hexanes) to afford the title compound. 1H NMR (600 MHz, CDCl3) δ 8.80 (d, 1H); 8.52 (d, 1H); 8.21 (d, 1H); 7.73 (dd, 1H); 7.60 (d, 1H); 7.32 (d, 1H); 7.27 (d, 1H); 4.79 (t, 1H); 1.99 (s, 1H); 1.89-1.79 (m, 2H); 0.94 (t, 3H). LRMS (APCI) calc'd for (C17H15ClNO2) [M+H]+, 300.1; found 300.1.

Workup

  1. customwas quenched via the addition of saturated aqueous ammonium chloride
  2. extractionThe mixture was extracted three times with dichloromethane
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified via flash chromatography (silica, 5-60% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-77545d0eb2ad41a59b2b00ce580aa63b
Source dataset
uspto-grants-2012_06
Patent number
US08207186B2

Reaction notes

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