Hydrochloric Acid → HCID 21099491, compound

HRID 2376947Notes

Reaction equation

HRID 2376947 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-3eb283d372a443309fea92ad22dadac1
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

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