Hydrochloric Acid → HCID 66668633, compound

HRID 1617858Notes

Reaction equation

HRID 1617858 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([C:12]2[CH:13]=[N:14][C:15]([O:18]C)=[CH:16][CH:17]=2)=[O:11])=[C:4]([F:20])[CH:3]=1.C[O:22][C:23]([C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)=[O:24].[C:34](=O)([O-])O.[Na+].Cl>O1CCOCC1.O.C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Rh].[Rh]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:28]2[CH:29]=[CH:30][C:25]([C:23]([OH:24])=[O:22])=[CH:26][CH:27]=2)[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15](=[O:18])[N:14]([CH3:34])[CH:13]=2)=[O:11])=[C:4]([F:20])[CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 27343694-Methoxycarbonylphenylboronic acidHCID 67015779HCID 67015779, compound

Product 1

HCID 66668633HCID 66668633, compound

Reagents, catalysts & solvents 3

HCID 6436379Rhodium, di-mu-chlorobis((1,2,5,6-eta)-1,5-cyclooctadiene)di-CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

In analogy to example 203, step 1, (E)-3-(4-chloro-2-fluorophenyl)-1-(6-methoxypyridin-3-yl)prop-2-en-1-one (example 237, step 1) was reacted with 4-methoxycarbonylphenylboronic acid in the presence of chloro(1,5-cyclooctadiene)rhodium(I) dimer and sodium hydrogen-carbonate in 1,4-dioxane and water at 60° C. The product of this reaction could not be obtained pure and was reacted in analogy to example 162, step 2 with concentrated aqueous HCl in 1,4-dioxane to give a light yellow solid which was used in the next step without purification. In analogy to example 161, step 1, the compound was reacted with iodomethane in the presence of potassium carbonate. In analogy to example 169, step 2, the methyl ester was hydrolyzed to give the title compound as an off-white solid, which was purified by extraction. MS (ESI−): m/z=412.0 [M−H]−.

Workup

  1. customThe product of this reaction could not
  2. custombe obtained pure
  3. customto give a light yellow solid which
  4. customwas used in the next step without purification
  5. customIn analogy to example 161, step 1, the compound was reacted with iodomethane in the presence of potassium carbonate

Sources & evidence

ORD record
ord-3ed7c4eb9e7043f3aa6b46edf046f904
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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