Acetone → HCID 59159266, compound

HRID 1096286Notes

Reaction equation

HRID 1096286 reaction equation
[OH:1][C@@H:2]1[CH2:9][N:8]([CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21](I)[CH:20]=3)[CH:15]([CH3:26])[C:14]2=[O:27])[CH2:7][CH2:6][C:3]21[CH2:5][CH2:4]2.[C:28]1(B(O)O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+].CC(C)=O>CC([O-])=O.CC([O-])=O.[Pd+2].O>[C:21]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:22]=[CH:23][CH:24]=[C:19]([N:16]2[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][CH2:10][N:8]3[CH2:7][CH2:6][C:3]4([CH2:5][CH2:4]4)[C@H:2]([OH:1])[CH2:9]3)[C:14](=[O:27])[CH:15]2[CH3:26])[CH:20]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 59159280HCID 59159280, compound

Product 1

HCID 59159266HCID 59159266, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 1-[3-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-propyl]-4-(3-iodo-phenyl)-3-methyl-piperazin-2-one (example 89; 60 mg, 0.12 mmol), phenylboronic acid (16 mg, 0.13 mmol), potassium carbonate (43 mg, 0.31 mmol), Pd(OAc)2 (0.6 mg, 2 μmol), acetone (0.5 mL), and water (0.6 mL) was heated at 65° C. for 30 min, then partitioned between CH2Cl2 and sat. aq. NaHCO3 solution. The organic layer was dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; EtOAc/MeOH 19:1) afforded the title compound (51 mg, 95%). Colorless gum, MS: 434.4 (M+H)+.

Workup

  1. custompartitioned between CH2Cl2 and sat. aq. NaHCO3 solution
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-cdc9888ef49a4b93b87b54755c69f4e1
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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