Sodium borohydride → 2-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]ethanol

HRID 1512825Notes

Reaction equation

HRID 1512825 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[N:24]([CH3:26])[CH:23]=[C:22]4[CH2:27][CH:28]=[O:29])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[BH4-].[Na+]>C1COCC1.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[N:24]([CH3:26])[CH:23]=[C:22]4[CH2:27][CH2:28][OH:29])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 59146184HCID 59146184, compound

Product 1

HCID 591461812-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]ethanolYield 89.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of [7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]acetaldehyde (D88) (500 mg) in THF (15 mL) and ethanol (15 mL) was added sodium borohydride (185 mg) in portion during 5 mins. The reaction mixture was stirred at 20° C. for 2 h. The reaction mixture was partitioned between ethyl acetate (50 mL) and water (50 mL). The organic phase was washed with water, 2 M hydrochloric acid and saturated brine, dried over sodium sulphate and evaporated to give the crude product as an off-white gum, which was purified by ISCO (10% ethyl acetate in hexanes) to afford 2-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]ethanol (D126) (450 mg). MS (ES): C22H22ClN3O3 requires 411; found 412.1 (M+H+).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (50 mL) and water (50 mL)
  2. washThe organic phase was washed with water, 2 M hydrochloric acid and saturated brine
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customto give the crude product as an off-white gum, which
  6. customwas purified by ISCO (10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-9dc59ae27ef54e409f31964f1e1c09dd
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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