Methanol → HCID 70274730, compound

HRID 2293481Notes

Reaction equation

HRID 2293481 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. Anal. Calc. C23H25N2 O3SF·0.5M H2O: C, 63.14; H, 5.99; N, 6.40. Found: C, 63.31; H, 5.94; N, 6.29.

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

Sources & evidence

ORD record
ord-c1e631b95b284acab2b7a3c63991ba6f
Source dataset
uspto-grants-1997_11
Patent number
US05686470

Reaction notes

Loading…