Methanol → HCID 70274730, compound

HRID 1416973Notes

Reaction equation

HRID 1416973 reaction equation
B.O1CCCC1.[CH2:7]([O:11][C:12]1[C:17]([C:18]#[N:19])=[CH:16][C:15]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[C:14]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[N:13]=1)[CH2:8][CH2:9][CH3:10].CO>O1CCCC1>[CH2:7]([O:11][C:12]1[C:17]([CH2:18][NH2:19])=[CH:16][C:15]([C:20]2[CH:21]=[CH:22][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:24][CH:25]=2)=[C:14]([C:30]2[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=2)[N:13]=1)[CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 2723981Borane;tetrahydrofuran2×HCID 53731292HCID 53731292, compound

Product 1

HCID 70274730HCID 70274730, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-tetrahydrofuran (1.0M in tetrahydrofuran, 1.5 mL, 0.0016 mole) was added by syringe to a solution of 2-butoxy-6-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]pyridine-3-carbonitrile (Example 14) (0.68 g, 0.0016 mole) in tetrahydrofuran (100 mL). After stirring at room temperature for 1 hour the solution was heated to reflux for 20 hours. Additional borane-tetrahydrofuran (2.4 mL) was added in three portions over the next 3 hours to the hot solution and stirred for 1 hour before cooling to room temperature. Methanol (20 mL) was added and the solution was concentrated to an oily solid. The product was purified by silica gel chromatography (Example 29) (128 mg, 0.3 mMol) in dimethylformamide after hydroxymethyl-5-[4-(methylsulfonyl)phenyl]pyridine.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 20 hours
  3. stirringstirred for 1 hour
  4. temperaturebefore cooling to room temperature
  5. concentrationthe solution was concentrated to an oily solid
  6. customThe product was purified by silica gel chromatography (Example 29) (128 mg, 0.3 mMol) in dimethylformamide after hydroxymethyl-5-[4-(methylsulfonyl)phenyl]pyridine

Sources & evidence

ORD record
ord-4ba9d65f730747b3bf87638c1c5331cc
Source dataset
uspto-grants-1999_06
Patent number
US05916905

Reaction notes

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