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Cesium carbonate → 6-Chloro-2-methyl-4-(5-methylisoxazol-3-ylamino)pyridazin-3(2H)-one

HRID 407755
Notes
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Reaction equation

HRID 407755 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([NH2:7])[CH:3]=1.Br[C:9]1[C:10](=[O:17])[N:11]([CH3:16])[N:12]=[C:13]([Cl:15])[CH:14]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[Cl:15][C:13]1[CH:14]=[C:9]([NH:7][C:4]2[CH:3]=[C:2]([CH3:1])[O:6][N:5]=2)[C:10](=[O:17])[N:11]([CH3:16])[N:12]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 661723-Amino-5-methylisoxazoleHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 592164744-Bromo-6-chloro-2-methyl-2,3-dihydropyridazin-3-one

Product 1

HCID 866840236-Chloro-2-methyl-4-(5-methylisoxazol-3-ylamino)pyridazin-3(2H)-oneYield 44%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 1,4-dioxane (40 mL), 5-methylisoxazol-3-amine (559 mg, 5.7 mmol), 4-bromo-6-chloro-2-methylpyridazin-3(2H)-one (1.89 g, 8.55 mmol), Pd2(dba)3 (521 mg, 0.57 mmol), XantPhos (329 mg, 0.57 mmol), and cesium carbonate (3.72 g, 11.4 mmol). After three cycles of vacuum/argon flush, the mixture was heated at 100° C. for 3 h. Then the mixture was cooled to 80° C. and filtered. The filtrate was cooled to room temperature. It was then filtered to afford 141a (600 mg, 44%) as a yellow solid. MS-ESI: [M+H]+ 241.0

Workup

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
  2. customAfter three cycles of vacuum/argon flush
  3. temperatureThen the mixture was cooled to 80° C.
  4. filtrationfiltered
  5. temperatureThe filtrate was cooled to room temperature
  6. filtrationIt was then filtered

Sources & evidence

ORD record
ord-2a70f2defe5a4befad73c1517ed55481
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08754077B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes