Cesium carbonate → HCID 89962119, compound

HRID 337842Notes

Reaction equation

HRID 337842 reaction equation
CC1(C)C(C)(C)OB([C:9]2[C:10]3([CH2:15][CH2:16][CH2:17][CH:18]=2)[O:14][CH2:13][CH2:12][O:11]3)O1.Br[C:21]1[CH:26]=[C:25]([Cl:27])[N:24]=[N:23][C:22]=1[NH2:28].C(=O)([O-])[O-].[Cs+].[Cs+].O1CCOCC1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[Cl:27][C:25]1[N:24]=[N:23][C:22]([NH2:28])=[C:21]([C:9]2[C:10]3([CH2:15][CH2:16][CH2:17][CH:18]=2)[O:11][CH2:12][CH2:13][O:14]3)[CH:26]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 220244193-Amino-4-bromo-6-chloropyridazineHCID 899634516-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,4-dioxaspiro[4.5]dec-6-ene

Product 1

HCID 89962119HCID 89962119, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 39a by using the 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,4-dioxaspiro[4.5]dec-6-ene (0.64 g, 2.40 mmol) prepared in Example 82a, 4-bromo-6-chloropyridazin-3-amine (0.50 g, 2.40 mmol), tetrakis(triphenylphosphine)palladium (0) (0.14 g, 0.12 mmol), cesium carbonate (1.72 g, 5.29 mmol), dioxane (8.0 mL) and water (4.0 mL), to yield the title compound (275.7 mg, 43%) as a colorless oil.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-4e8760d21a7944e6a9304d36acc17e4a
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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