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

HRID 1512787
Notes
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Reaction equation

HRID 1512787 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.[Cl:13][C:14]1[CH:15]=[C:16]([C:24]2[O:28][N:27]=[C:26]([C:29]3[CH:30]=[CH:31][CH:32]=[C:33]4[C:37]=3[N:36]([CH3:38])[CH:35]=[C:34]4[CH:39]=O)[N:25]=2)[CH:17]=[CH:18][C:19]=1[O:20][CH:21]([CH3:23])[CH3:22].[OH-].[Na+]>C(O)C>[Cl:13][C:14]1[CH:15]=[C:16]([C:24]2[O:28][N:27]=[C:26]([C:29]3[CH:30]=[CH:31][CH:32]=[C:33]4[C:37]=3[N:36]([CH3:38])[CH:35]=[C:34]4[CH2:39][N:2]3[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]3)[N:25]=2)[CH:17]=[CH:18][C:19]=1[O:20][CH:21]([CH3:22])[CH3:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 18521570Ethyl 4-piperidinecarboxylate hydrochlorideHCID 591461277-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indole-3-carbaldehyde

Product 1

HCID 59146087Ethyl 1-{[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]methyl}-4-piperidinecarboxylateYield 57.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-piperidinecarboxylate hydrochloride (969 mg) and 7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indole-3-carbaldehyde (D61) (396 mg) was added to a solution of NaOH (200 mg) in ethanol (10 mL). After stirring for 0.5 hour, ethanol was evaporated off and then dichloromethane (40 mL) containing AcOH (0.5 mL) was added to the residue. NaBH(OAc)3 (1.06 g) was added to the above mixture. The reaction mixture was stirred at room temperature overnight and then terminated by saturated NaHCO3 solution. The organic layer was separated and washed with water and brine. After the solvent was evaporated off the residue was purified by Mass Directed AutoPrep to afford ethyl 1-{[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]methyl}-4-piperidinecarboxylate (D79) (308 mg) as a yellow solid. MS (ES): C29H33ClN4O4 requires 536; found 537.3 (M+H+).

Workup

  1. customethanol was evaporated off
  2. additiondichloromethane (40 mL) containing AcOH (0.5 mL)
  3. additionwas added to the residue
  4. additionNaBH(OAc)3 (1.06 g) was added to the above mixture
  5. stirringThe reaction mixture was stirred at room temperature overnight
  6. customterminated by saturated NaHCO3 solution
  7. customThe organic layer was separated
  8. washwashed with water and brine
  9. customAfter the solvent was evaporated off the residue
  10. customwas purified by Mass Directed AutoPrep

Sources & evidence

ORD record
ord-51da6a158cb440c096dc80d13d96763f
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08217028B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes