Sodium Bicarbonate → HCID 66668773, compound

HRID 1617873Notes

Reaction equation

HRID 1617873 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([C:12]2[CH:13]=[CH:14][C:15](=[O:19])[N:16]([CH3:18])[CH:17]=2)=[O:11])=[C:4]([F:20])[CH:3]=1.[OH:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.C(=O)([O-])O.[Na+]>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:26]2[CH:27]=[CH:28][C:23]([CH2:22][OH:21])=[CH:24][CH:25]=2)[CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15](=[O:19])[N:16]([CH3:18])[CH:17]=2)=[O:11])=[C:4]([F:20])[CH:3]=1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 66668501HCID 66668501, compound

Product 1

HCID 66668773HCID 66668773, compound

Reagents, catalysts & solvents 3

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

Procedure

In analogy to example 203, step 1, (E)-5-(3-(4-chloro-2-fluorophenyl)acryloyl)-1-methylpyridin-2(1H)-one (example 314, step 2) was reacted with 4-(hydroxymethyl)phenyl-boronic acid in the presence of chloro(1,5-cyclooctadiene)rhodium (I) dimer and sodium hydrogencarbonate in 1,4-dioxane and water at 60° C. to give the title compound as a colourless foam, MS (ESI+): m/z=400.2 [M+H]+.

Sources & evidence

ORD record
ord-be91f3070ec749e29bb5db12c1c0513d
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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