Hydrochloric Acid → HCID 21099491, compound

HRID 1351632Notes

Reaction equation

HRID 1351632 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]#N)[CH:21]=2)(=[O:19])=[O:18])=[CH:13][N:12]=1.[H-].C([Al+]CC(C)C)C(C)C.C[OH:39].Cl>ClCCl.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]1[N:12]=[CH:13][C:14]([S:17]([C:20]2[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=2)[CH:26]=[O:39])(=[O:19])=[O:18])=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 21099467HCID 21099467, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 21099491HCID 21099491, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 2-[(E)-2-(2,4-difluorophenyl)vinyl]-5-[(3-cyanophenyl)-sulfonyl]pyridine (Example 33, 200 mg, 0.52 mmol) in dichloromethane (2 mL) and toluene (2 mL) was cooled in an ice-bath while stirring under nitrogen. Diisobutylaluminium hydride (1.5M in toluene, 0.38 mL, 0.57 mmol) was added and the reaction stirred at 0° C. then allowed to warm to room temperature over 3 hours. Methanol was added then 1N aqueous hydrochloric acid and the mixture left to stand overnight. The products were extracted into dichloromethane, dried over MgSO4 and concentrated in vacuo. Dry flash column chromatography using 3% methanol/dichloromethane followed by recrystallisation from methanol gave 3-({6-[(E)-2-(2,4-difluorophenyl)vinyl]pyridin-3-yl}sulfonyl)benzaldehyde (93 mg, 46%). δH (400 MHz, CDCl3): 9.07 (1H, d, J=2.2 Hz), 8.23–8.09 (3H, m), 7.89–7.81 (2H, m), 7.74–7.66 (1H, m), 7.61–7.55 (1H, m), 7.48–7.44 (1H, m), 7.25–7.16 (2H, m), 6.93–6.83 (2H, m); m/z (ES+) 386 [MH+].

Workup

  1. temperaturewas cooled in an ice-bath
  2. stirringthe reaction stirred at 0° C.
  3. extractionThe products were extracted into dichloromethane
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customDry flash column chromatography
  7. customfollowed by recrystallisation from methanol

Sources & evidence

ORD record
ord-b72c68cc47ee48d881db3edfb6a97bfe
Source dataset
uspto-grants-2007_05
Patent number
US07217740B2

Reaction notes

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