Potassium Iodide → HCID 86654534, compound

HRID 2382582Notes

Reaction equation

HRID 2382582 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH2:13][NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[CH:6]=[O:7].[I-].[K+]>CN(C=O)C.O>[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[N:14]1[CH2:2][C:3]2[CH:4]=[C:5]([CH:6]=[O:7])[CH:8]=[CH:9][C:10]=2[O:11][CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 4875Potassium IodideHCID 87320691HCID 87320691, compound2×

Product 1

HCID 86654534HCID 86654534, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 3-chloromethyl-4-[2-(pyridin-2-yl-amino)-ethoxy]-benzaldehyde [compound of step II] (7.45 g, 25.7 mmol) in 340 mL DMF, was added potassium iodide (8.53 g, 51.4 mmol) and the reaction mixture was heated to 130° C. for 1 hour. The reaction mixture was cooled, diluted with 1 L water and extracted with 2×500 mL of ethyl acetate. The ethyl acetate extract was washed with 250 mL brine, dried over anhydrous sodium sulfate and concentrated under vacuum at 40° C. to give 5.9 g crude material. This crude material was purified by silica chromatography using 15% ethyl acetate in petroleum ether to give 4-pyridin-2-yl-2,3,4,5-tetrahydro-benzo [f][1,4]oxazepine-7-carbaldehyde.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with 2×500 mL of ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washwas washed with 250 mL brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum at 40° C.
  7. customto give 5.9 g crude material
  8. customThis crude material was purified by silica chromatography

Sources & evidence

ORD record
ord-37c132e2ece048cd9b31799589ac2210
Source dataset
uspto-grants-2012_09
Patent number
US08263587B2

Reaction notes

Loading…