Sodium Carbonate → HCID 67398475, compound

HRID 12971Notes

Reaction equation

HRID 12971 reaction equation
[CH3:1][N:2]1[CH2:9][C@@H:8]2[C@@H:4]([N:5]([C:10]3[CH:15]=[CH:14][C:13](B4OC(C)(C)C(C)(C)O4)=[CH:12][CH:11]=3)[CH2:6][CH2:7]2)[CH2:3]1.Br[C:26]1[CH:27]=[CH:28][C:29]([N:32]2[C:37](=[O:38])[CH:36]=[CH:35][CH:34]=[N:33]2)=[N:30][CH:31]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.C([O-])([O-])=O.[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][N:2]1[CH2:9][C@@H:8]2[C@H:4]([N:5]([C:10]3[CH:11]=[CH:12][C:13]([C:26]4[CH:27]=[CH:28][C:29]([N:32]5[C:37](=[O:38])[CH:36]=[CH:35][CH:34]=[N:33]5)=[N:30][CH:31]=4)=[CH:14][CH:15]=3)[CH2:6][CH2:7]2)[CH2:3]1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 59339917HCID 59339917, compoundHCID 59339926HCID 59339926, compound

Product 1

HCID 67398475HCID 67398475, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
140 °C

Procedure

(3aR,6aR)-5-Methyl-1-(4-(4,4,5,5-tetramethyl-1,3-dioxaborolan-2-yl)phenyl)octa-hydro-pyrrolo[3,4-b]pyrrole (50 mg, 0.15 mmol), 2-(5-bromopyridin-2-yl)pyridazin-3(2H)-one (42 mg, 0.17 mmol), Pd(PPh3)2Cl2 (11 mg, 0.01 mmol), 2-(dicyclohexylphosphino)biphenyl (5.6 mg, 0.016 mmol) and Na2CO3 (1M, 225 μL) were placed in a microwave tube, purged with N2 and a mixture of solvents (EtOH:dioxane=1:1, 1 mL) was added. The mixture was heated to 140° C. in a microwave reactor for 15 minutes, cooled to ambient temperature, was filtered, and concentrated under reduced pressure. The residue was purified via chromatography (SiO2, 0-10% MeOH in CH2Cl2) to provide the title compound, 1H NMR (300 MHz, CDCl3): δ=8.82 ppm (d, J=2.8 Hz, 1H), 7.98 (m, 2H), 7.73 (d, J=8.2 Hz, 1H), 7.52 (m, 2H), 7.28 (dd, J=10.1, 3.7 Hz, 1H), 7.09 (dd, J=10.1, 1.7 Hz, 1H), 6.67 (m, 2H), 4.39 (m, 1H), 3.66 (m, 1H), 3.30 (m, 3H), 2.87 (m, 2H), 2.59 (s(br), 3H), 2.23 (m, 2H), 2.05 (m, 1H). MS (ESI, M+1): 374.2.

Workup

  1. custompurged with N2
  2. additiona mixture of solvents (EtOH:dioxane=1:1, 1 mL)
  3. additionwas added
  4. temperaturecooled to ambient temperature
  5. filtrationwas filtered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified via chromatography (SiO2, 0-10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-900395d3d32c49ffa4012aa0f8903ebd
Source dataset
uspto-grants-2010_06
Patent number
US07728031B2

Reaction notes

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