Sodium borohydride → HCID 59146044, compound

HRID 1512802Notes

Reaction equation

HRID 1512802 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[NH:24][CH:23]=[C:22]4[CH2:26][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+]>>[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[NH:24][CH:23]=[C:22]4[CH2:26][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

3

Reactant 2

HCID 4311764Sodium borohydrideHCID 59146073HCID 59146073, compound

Product 1

HCID 59146044HCID 59146044, compoundYield 92.9%

Conditions

Temperature
20 °C

Procedure

To a solution of 3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanal (D92) (300 mg) was added NaBH4 (138 mg). The reaction mixture was stirred at 20° C. overnight. The reaction mixture was evaporated and the residue was partitioned between DCM (50 mL) and water (25 mL). The organic phase was washed with water and brine, dried over sodium sulphate and evaporated in vacuo to afford the product 3-[7-(5-{3-chloro-4-[(1-methyl ethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]-1-propanol as a white solid (D99) (280 mg). MS (ES): C22H22ClN3O3 requires 411; found 412.2 (M+H+).

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was partitioned between DCM (50 mL) and water (25 mL)
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over sodium sulphate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-c4f9f74e86f642ce86a33446b9d769cd
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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