Methanol → HCID 9884617, compound

HRID 1057662Notes

Reaction equation

HRID 1057662 reaction equation
[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:21][CH2:22][C:23]#[N:24])[C:15]=2[C:14]2[C:9]1=[CH:10][C:11]([O:25][CH3:26])=[CH:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO>C1COCC1>[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([O:21][CH2:22][CH2:23][NH2:24])[C:15]=2[C:14]2[C:9]1=[CH:10][C:11]([O:25][CH3:26])=[CH:12][CH:13]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 887Methanol2×HCID 18671671[(9-Benzyl-7-methoxy-9H-carbazol-4-yl)oxy]acetonitrile

Product 1

HCID 9884617HCID 9884617, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of [(9-benzyl-7-methoxy-9H-carbazol-4-yl)oxy]acetonitrile (0.9 g, 2.6 mmol) in dry THF (50 mL) is added borane-methylsulfide complex (0.75 mL, 7.9 mmol). The mixture is heated at 40° C. overnight. Methanol is slowly added to mixture until addition of methanol did not evolve gas. The solvents are removed under reduced pressure. Methanol (50 mL) is added to the residue then removed under reduced pressure. Methanol (100 mL) and concentrated hydrochloric acid (3 mL) is added to the residue. The mixture is heated at 75° C. for 2.5 h. The mixture is neutralized with saturated potassium carbonate and partitioned between water and ethyl acetate. The layers are separated and the organic layer washed twice with brine. The organic layer is dried over anhydrous sodium sulfate, filtered, and concentrated. Column chromatography, silica gel (100 mL) using CH2Cl2: CH3OH (95:5) as eluent gave 0.52 g (58%) of the title compound; 1H NMR (DMSO-d6) δ2.48, 3.8, 4.12, 5.59, 6.69, 6.8, 7.14, 7.2, 8.03; Anal. Calcd for C22H22N2O2: C, 76.28; H, 6.40; N, 8.09. Found: C, 76.00; H, 6.54; N, 7.92.

Workup

  1. additionis added borane-methylsulfide complex (0.75 mL, 7.9 mmol)
  2. customThe solvents are removed under reduced pressure
  3. additionMethanol (50 mL) is added to the residue
  4. customthen removed under reduced pressure
  5. additionMethanol (100 mL) and concentrated hydrochloric acid (3 mL) is added to the residue
  6. temperatureThe mixture is heated at 75° C. for 2.5 h
  7. custompartitioned between water and ethyl acetate
  8. customThe layers are separated
  9. washthe organic layer washed twice with brine
  10. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-3fd934a8df21413d88b445482b5f48d5
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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