Carbon Dioxide → HCID 68638237, compound

HRID 2234115Notes

Reaction equation

HRID 2234115 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].[CH3:33][N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+].C(=O)=O>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:37]3[CH2:38][CH2:39][N:34]([CH3:33])[CH2:35][CH2:36]3)[CH:15]=2)[CH:10]=[C:9]1[C:19]1[CH:24]=[C:23]([C:25]2[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=2)[N:22]=[N:21][C:20]=1[O:31][CH3:32])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86612052HCID 86612052, compound

Product 1

HCID 68638237HCID 68638237, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

293 mg 6-Formyl-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester (see example 119) is dissolved in 52 mL dichloromethane. 635 □L N-methylpiperazine and then 2.6 mL acetic acid are added. 656 mg sodium triacetoxyborohydride is added in several portions over 3 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. 344 mg (100%) 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-33735355382c439b96f245c2233fb1f0
Source dataset
uspto-grants-2010_05
Patent number
US07709466B2

Reaction notes

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