Ammonium Chloride → HCID 86703303, compound

HRID 2409986Notes

Reaction equation

HRID 2409986 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:18][C:19]3[N:24]=[C:23]([C:25](OC)=[O:26])[CH:22]=[CH:21][CH:20]=3)=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:9]2)=[CH:5][CH:4]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO.O1CCCC1>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:18][C:19]3[N:24]=[C:23]([CH2:25][OH:26])[CH:22]=[CH:21][CH:20]=3)=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:9]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 50903302HCID 50903302, compound

Product 1

HCID 86703303HCID 86703303, compoundYield 104.5%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of methyl 6-(6-methoxy-2-phenyl-1H-indol-3-ylmethyl)pyridine-2-carboxylate (1.2 g) in methanol/tetrahydrofuran (6 mL/6 mL) was added sodium borohydride (305 mg) at room temperature. The mixture was stirred at room temperature for 3.5 hours. To the reaction mixture was added a saturated aqueous ammonium chloride solution. The organic layer was separated, washed with a saturated aqueous ammonium chloride solution and saturated brine successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain the title compound (1.16 g). 1H-NMR (CDCl3) δ ppm: 3.86 (3H, s), 4.00-4.10 (1H, m), 4.41 (2H, s), 4.70-4.78 (2H, m), 6.76 (1H, dd, J=2.3, 8.8 Hz), 6.91 (1H, d, J=2.3 Hz), 6.96-7.04 (2H, m), 7.31-7.38 (2H, m), 7.39-7.59 (5H, m), 8.05 (1H, br s).

Workup

  1. customThe organic layer was separated
  2. washwashed with a saturated aqueous ammonium chloride solution and saturated brine successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-742a72b2889b4a4cace79645209f5576
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

Loading…