Water → HCID 89714538, compound

HRID 2273076Notes

Reaction equation

HRID 2273076 reaction equation
[CH2:1]([N:3]1[CH2:9][C:8]([CH3:11])([CH3:10])[O:7][C:6]2[N:12]=[C:13]([N:24]3[CH2:30][CH:29]4[O:31][CH:26]([CH2:27][CH2:28]4)[CH2:25]3)[N:14]=[C:15](OS(C(F)(F)F)(=O)=O)[C:5]=2[C:4]1=[O:32])[CH3:2].CC1(C)C(C)(C)OB([C:41]2[CH:42]=[CH:43][C:44]([NH2:47])=[N:45][CH:46]=2)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>O1CCOCC1.C(OCC)(=O)C.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>[NH2:47][C:44]1[N:45]=[CH:46][C:41]([C:15]2[C:5]3[C:4](=[O:32])[N:3]([CH2:1][CH3:2])[CH2:9][C:8]([CH3:10])([CH3:11])[O:7][C:6]=3[N:12]=[C:13]([N:24]3[CH2:25][CH:26]4[O:31][CH:29]([CH2:28][CH2:27]4)[CH2:30]3)[N:14]=2)=[CH:42][CH:43]=1

Participants

8

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 89714539HCID 89714539, compound

Product 1

HCID 89714538HCID 89714538, compoundYield 79.9%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

170 mg (353.83 μmol) of trifluoromethanesulfonic acid 6-ethyl-8,8-dimethyl-2-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-5-oxo-5,6,7,8-tetrahydro-9-oxa-1,3,6-triazabenzocyclohepten-4-yl ester and 90.16 mg (389.21 μmol) of 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridin-2-ylamine are dissolved in 3 ml of dioxane in a microwave tube. 150.21 mg (707.66 μmol) of tripotassium phosphate and 1 ml of water are added The solution is purged with argon. Finally, 24.84 mg (35.38 μmol) of bis(triphenylphosphine)palladium(II) chloride are added and the mixture is heated in a Biotage microwave machine for 15 minutes at 100° C. The reaction mixture is diluted in ethyl acetate and washed with water and then with saturated NaCl solution. The precipitate present in the organic phase is filtered off to give 120 mg of 4-(6-aminopyridin-3-yl)-6-ethyl-8,8-dimethyl-2-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-7,8-dihydro-6H-9-oxa-1,3,6-triazabenzocyclohepten-5-one.

Workup

  1. customis purged with argon
  2. washwashed with water
  3. filtrationThe precipitate present in the organic phase is filtered off

Sources & evidence

ORD record
ord-b227d3f442784745b6bdfb46417686ba
Source dataset
uspto-grants-2015_09
Patent number
US09120812B2

Reaction notes

Loading…