Water → HCID 57299675, compound

HRID 1416972Notes

Reaction equation

HRID 1416972 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]([O:15][C:16]1[C:21]([C:22]#N)=[CH:20][C:19]([C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=2)=[C:18]([C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)[N:17]=1)[CH2:12][CH2:13][CH3:14].[OH2:41]>C1(C)C=CC=CC=1.CO>[CH2:11]([O:15][C:16]1[C:21]([CH:22]=[O:41])=[CH:20][C:19]([C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:31])=[O:32])=[CH:26][CH:25]=2)=[C:18]([C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)[N:17]=1)[CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 3

HCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 53731292HCID 53731292, compound

Product 1

HCID 57299675HCID 57299675, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 1140TolueneSolvent

Procedure

Diisobutyl aluminum hydride (1.0M in toluene, 3 mL, 3 mMol) was added in three portions over 26 hours (0 hours, 24 hours, 26 hours) to a solution of 2-butoxy-6-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]pyridine-3-carbonitrile, Example 14, (0.42 gm, 1 mMol) in toluene (75 mL) and stirred at room temperature. Methyl alcohol (5 mL) was added dropwise followed by a solution of water (5 mL) in methyl alcohol (25 mL). The layers were separated and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to a semi-solid. The products were separated and purified by silica gel chromatography. Example 29 Anal. Calc'd. C23H24NO4SF: C, 64.32; H, 5.63; N, 3.26. Found: C, 64.27; H, 5.59; N, 3.23. Example 30 Anal. Calc'd. C23H22NO4SF: C, 64.62; H, 5.19; N, 3.28. Found: C, 64.84; H, 5.39; N, 3.58.

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to a semi-solid
  5. customThe products were separated
  6. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-b4ec4e181025449e9c00f4fc2b0aaf4a
Source dataset
uspto-grants-1999_06
Patent number
US05916905

Reaction notes

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