Carbon Dioxide → HCID 67148781, compound

HRID 1786701Notes

Reaction equation

HRID 1786701 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH:17]=O)[CH:15]=2)[CH:10]=[C:9]1[C:19]1[CH:24]=[C:23]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[N:22]=[N:21][C:20]=1[O:31][CH3:32])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+].C(=O)=O>ClC(Cl)C.ClCCl.C(O)(=O)C>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][N:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)[CH:15]=2)[CH:10]=[C:9]1[C:19]1[CH:24]=[C:23]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[N:22]=[N:21][C:20]=1[O:31][CH3:32])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

9

Reactant 5

HCID 280Carbon DioxideHCID 8082PiperidineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86612052HCID 86612052, compound

Product 1

HCID 67148781HCID 67148781, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

79 mg 6-formyl-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester is dissolved in 14 mL dichloroethane. 182 mL piperidine and then 0.7 mL acetic acid are added. 334 mg sodium triacetoxyborohydride is added in several portions over 6 hours. Sat. aq. NaHCO3-solution is added and the reaction mixture is stirred until the CO2-evolution stopped. The reaction mixture is diluted with dichloromethane, the aq. phase washed with dichloromethane, the combined org. phases dried (MgSO4) and concentrated in vacuo. 76 mg (83%) crude product is obtained, which is directly used in the next step.

Workup

  1. washthe aq. phase washed with dichloromethane
  2. dry with materialphases dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-16e15281ca544ab5b7ef7ac523cb9677
Source dataset
uspto-grants-2009_03
Patent number
US07507734B2

Reaction notes

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