Sodium Carbonate → HCID 86630727, compound

HRID 547788Notes

Reaction equation

HRID 547788 reaction equation
[CH3:1][C:2]1[C:7](OS(C(F)(F)F)(=O)=O)=[CH:6][CH:5]=[CH:4][N:3]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+].[F:39][C:40]([F:74])([F:73])[C:41]1[CH:42]=[C:43]([C:51]([CH3:72])([CH3:71])[C:52]([N:54]([C:56]2[CH:57]=[N:58][C:59]([N:63]3[CH2:67][C@H:66]([OH:68])[CH2:65][C@H:64]3[CH2:69][OH:70])=[CH:60][C:61]=2I)[CH3:55])=[O:53])[CH:44]=[C:45]([C:47]([F:50])([F:49])[F:48])[CH:46]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.O.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[F:50][C:47]([F:48])([F:49])[C:45]1[CH:44]=[C:43]([C:51]([CH3:71])([CH3:72])[C:52]([N:54]([C:56]2[CH:57]=[N:58][C:59]([N:63]3[CH2:67][C@H:66]([OH:68])[CH2:65][C@H:64]3[CH2:69][OH:70])=[CH:60][C:61]=2[C:7]2[C:2]([CH3:1])=[N:3][CH:4]=[CH:5][CH:6]=2)[CH3:55])=[O:53])[CH:42]=[C:41]([C:40]([F:74])([F:39])[F:73])[CH:46]=1

Participants

9

Reactant 5

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 107764652-Methylpyridin-3-yl trifluoromethanesulfonateHCID 86597685HCID 86597685, compound

Product 1

HCID 86630727HCID 86630727, compoundYield 39%

Reagents, catalysts & solvents 3

HCID 53485975CID 53485975CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 0.12 g (0.48 mmol) trifluoro-methanesulfonic acid 2-methyl-pyridin-3-yl ester, 0.13 g (0.52 mmol) bis(pinacolato)diboron, 0.14 g (1.4 mmol) potassium acetate and 0.02 g (0.02 mmol) dichloro[1,1′-bis(diphenylphosphino) ferrocene]palladium(II) dichloromethane adduct in 2.5 ml N,N-dimethylformamide was heated at 80° C. over night under argon. After cooling to room temperature 0.10 g (0.16 mmol) (2S,4R)-2-(3,5-bis-trifluoromethyl-phenyl)-N-[6-(4-hydroxy-2-hydroxymethyl-pyrrolidin-1-yl)-4-iodo-pyridin-3-yl]-N-methyl-isobutyramide and 1.3 ml of a deoxygenated 2 M aqueous solution of sodium carbonate were added. The reaction mixture was heated at 80° C. for 6 h. After cooling to room temperature the mixture was diluted with water and extracted with three portions of tert-butyl methyl ether. The combined organic layers were dried over sodium sulfate and concentrated in vacuo. Flash column chromatography gave 37 mg (39%) of the title compound as an off-white solid.

Workup

  1. additionwere added
  2. temperatureThe reaction mixture was heated at 80° C. for 6 h
  3. temperatureAfter cooling to room temperature the mixture
  4. extractionextracted with three portions of tert-butyl methyl ether
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-768ac212a7714245935d6decf22121b5
Source dataset
uspto-grants-2011_05
Patent number
US07939533B2

Reaction notes

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