Sodium Carbonate → HCID 67976579, compound

HRID 1184795Notes

Reaction equation

HRID 1184795 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH:13]2[CH2:17][C:16]3[CH:18]=[C:19](B4OC(C)(C)C(C)(C)O4)[CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].Cl[C:32]1[N:37]=[N:36][C:35]([NH:38][C:39](=[O:41])[CH3:40])=[CH:34][CH:33]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH:13]2[CH2:17][C:16]3[CH:18]=[C:19]([C:32]4[N:37]=[N:36][C:35]([NH:38][C:39](=[O:41])[CH3:40])=[CH:34][CH:33]=4)[CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:9][CH2:8]1)=[O:6])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 19095604N-(6-Chloropyridazin-3-yl)acetamideHCID 67973765HCID 67973765, compound

Product 1

HCID 67976579HCID 67976579, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 4-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzofuran-2-yl]-piperidine-1-carboxylic acid isopropyl ester (41.5 mg) and N-(6-chloro-pyridazin-3-yl)-acetamide (25.7 mg) in dioxane (2 mL) a 2 M aqueous Na2CO3 solution (0.125 mL) is added. The mixture is sparged with argon for 10 min and (2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl)[2-(2-aminoethylphenyl)]palladium(11) chloride*methyl-t-butylether complex (CAS-number.: 1028206-58-7; 8 mg) is added. The resulting mixture is stirred for 1 h at 150° C. After cooling to room temperature, the mixture is filtered over basic alumina and eluted with N,N-dimethylformamide/MeOH (9:1; 2 mL). The solvent is evaporated and the residue is purified by preparative HPLC (eluent water (+0.1% NH3)/MeOH) to yield the desired product. HPLC (method 13): tR=0.26 min; Mass spectrum (ESI+): m/z=425 [M+H]+.

Workup

  1. additionis added
  2. customThe mixture is sparged with argon for 10 min
  3. addition(2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl)[2-(2-aminoethylphenyl)]palladium(11) chloride*methyl-t-butylether complex (CAS-number.: 1028206-58-7; 8 mg) is added
  4. temperatureAfter cooling to room temperature
  5. filtrationthe mixture is filtered over basic alumina
  6. washeluted with N,N-dimethylformamide/MeOH (9:1; 2 mL)
  7. customThe solvent is evaporated
  8. customthe residue is purified by preparative HPLC (eluent water (+0.1% NH3)/MeOH)

Sources & evidence

ORD record
ord-dbc9a962ffcb488d8c50594c334031ac
Source dataset
uspto-grants-2014_03
Patent number
US08669271B2

Reaction notes

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