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

HRID 1512789Notes

Reaction equation

HRID 1512789 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:20]=[CH:21][CH:22]=[C:23]4[C:27]=3[NH:26][CH:25]=[C:24]4/[CH:28]=[CH:29]/[N+:30]([O-:32])=[O:31])[N:15]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([CH3:13])[CH3:12]>O1CCOCC1.C(O)C>[Cl:3][C:4]1[CH:5]=[C:6]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:20]=[CH:21][CH:22]=[C:23]4[C:27]=3[NH:26][CH:25]=[C:24]4[CH2:28][CH2:29][N+:30]([O-:32])=[O:31])[N:15]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([CH3:12])[CH3:13]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 59146096HCID 59146096, compound

Product 1

HCID 591460297-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-3-(2-nitroethyl)-1H-indoleYield 84.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a suspension of NaBH4 (0.7 g) in 1,4-dioxane (150 mL) and ethanol (50 mL) stirred in air at room temperature was added a solution of 7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-3-[(E)-2-nitroethenyl]-1H-indole (D82) (2.6 g) in 1,4-dioxane (150 mL) dropwise. The reaction mixture was stirred at 20° C. for 1 h. The excess NaBH4 was quenched with dilute H2SO4. The reaction solution was concentrated. Ethyl acetate (300 mL) was added to the residue, washed with water and brine, and then dried over MgSO4. Solvent was evaporated off to give the desired product 7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-3-(2-nitroethyl)-1H-indole (D83) (2.2 g) as a yellow solid. δH (CDCl3, 400 MHz): 1.46 (6H, d), 3.55 (2H, t), 4.69-4.74 (3H, m), 7.07 (1H, d), 7.23 (1H, d), 7.30 (1H, t), 7.75 (1H, d), 8.08 (1H, dd), 8.12 (1H, d), 8.26 (1H, d), 9.74 (1H, s). MS (ES): C21H19ClN4O4 requires 426; found 427.2 (M+H+).

Workup

  1. stirringThe reaction mixture was stirred at 20° C. for 1 h
  2. customThe excess NaBH4 was quenched with dilute H2SO4
  3. concentrationThe reaction solution was concentrated
  4. additionEthyl acetate (300 mL) was added to the residue
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. customSolvent was evaporated off

Sources & evidence

ORD record
ord-1b82e9ccdab54c9e9357f612fde5ce76
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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