Toluene → HCID 58303086, compound

HRID 1891330Notes

Reaction equation

HRID 1891330 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].Cl[C:13]1[N:14]=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=1.C1(C)C=CC=CC=1.CC([O-])(C)C.[Na+]>CCOC(C)=O.O.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:13]2[N:14]=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 1140TolueneHCID 70770Ethyl 4-piperidinecarboxylateHCID 744033-Chloro-6-methoxypyridazineHCID 23676156Sodium t-butoxide

Product 1

HCID 58303086HCID 58303086, compoundYield 40.2%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

To a stirred solution of piperidine-4-carboxylic acid ethyl ester (5.66 g, 36.0 mmol) and 3-chloro-6-methoxy-pyridazine (4.34 g, 30 mmol) in toluene (60 mol) was added NaOtBu (3.46 g, 36 mol), BINAP (560 mg, 0.90 mmol) and tris(dibenilideneacetone)dipalladium(0) (549 mg, 0.60 mmol). The reaction mixture was heated at 95° C. for 1 hours, cooled down to RT, and diluted with AcOEt (500 mL) and H2O (50 mL). The organic layer was separated and washed with brine, dried over Na2SO4 and concentrated under vacuo. Column chromatography (SiO2, EtOAc/heptane, 1:9 to 1:1) yielded 3.20 g (34%) of 1-(6-methoxy-pyridazin-3-yl)-piperidine-4-carboxylic acid ethyl ester as a yellow oil. ES-MS m/e: 266.3 (M+H+).

Workup

  1. temperaturecooled down to RT
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-8fef12b6aded46d3b4ad71b431fb4f66
Source dataset
uspto-grants-2013_08
Patent number
US08507535B2

Reaction notes

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