Methanol → 3,5-Dichloro-4-(4-chloro-thiazolo[5,4-c]pyridin-2-yl)-benzaldehyde

HRID 2366222Notes

Reaction equation

HRID 2366222 reaction equation
[Cl:1][C:2]1[C:7]2[S:8][C:9]([C:11]3[C:16]([Cl:17])=[CH:15][C:14]([CH:18]=C)=[CH:13][C:12]=3[Cl:20])=[N:10][C:6]=2[CH:5]=[CH:4][N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C[OH:41]>C(Cl)Cl>[Cl:20][C:12]1[CH:13]=[C:14]([CH:15]=[C:16]([Cl:17])[C:11]=1[C:9]1[S:8][C:7]2[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][C:6]=2[N:10]=1)[CH:18]=[O:41]

Participants

5

Reactant 3

HCID 887MethanolHCID 11776TriphenylphosphineHCID 867233104-Chloro-2-(2,6-dichloro-4-vinyl-phenyl)-thiazolo[5,4-c]pyridine

Product 1

HCID 866690003,5-Dichloro-4-(4-chloro-thiazolo[5,4-c]pyridin-2-yl)-benzaldehydeYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-chloro-2-(2,6-dichloro-4-vinyl-phenyl)-thiazolo[5,4-c]pyridine (0.168 g, 0.48 mmol) in DCM (3.8 mL) and MeOH (1 mL) was cooled to −78° C. and degassed with nitrogen then compressed air before the ozone generator was turned on. After 10 minutes, a persistent grey colour remained so the ozone generator was turned off and the reaction mixture was degassed with nitrogen. Triphenylphosphine (0.125 g, 0.48 mmol) was added and the mixture warmed to ambient temperature and stirred for 1 hour. The reaction mixture was partitioned between DCM and water. The organic layer dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with 0-12% EtOAc in pentane to give the desired compound as an off-white solid (0.138 g, 84% yield). 1H NMR (300 MHz, CDCl3): δ 10.04 (s, 1H), 8.55 (d, J=5.6 Hz, 1H), 7.99-7.98 (m, 3H).

Workup

  1. customdegassed with nitrogen
  2. customthe reaction mixture was degassed with nitrogen
  3. customThe reaction mixture was partitioned between DCM and water
  4. dry with materialThe organic layer dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel flash chromatography
  7. washeluting with 0-12% EtOAc in pentane

Sources & evidence

ORD record
ord-9f074c320bd949439acdcbd6bb833ce6
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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