Lithium Chloride → HCID 59159283, compound

HRID 1096287Notes

Reaction equation

HRID 1096287 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([Sn](CCCC)(CCCC)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=1)CCC.[Cl-].[Li+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C)C=O>[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]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=4)[CH:20]=3)[CH:15]([CH3:26])[C:14]2=[O:27])[CH2:7][CH2:6][C:3]21[CH2:5][CH2:4]2

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 6077842-(Tributylstannyl)pyridineHCID 59159280HCID 59159280, compound

Product 1

HCID 59159283HCID 59159283, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °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; 80 mg, 0.17 mmol), 2-(tributylstannyl)pyridine (73 mg, 0.20 mmol), tetrakis(triphenylphosphine)palladium(0), lithium chloride (42 mg, 0.99 mmol) copper chloride (82 mg, 0.83 mmol), and N,N-dimethylformamide (3 mL) was heated at 100° C. for 16 h, then the reaction mixture was partitioned between CH2Cl2 and sat. aq. NaHCO3 solution. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; EtOAc-MeOH gradient) afforded the title compound (3.5 mg, 5%). Colorless gum, MS: 435.3 (M+H)+.

Workup

  1. customthe reaction mixture was partitioned between CH2Cl2 and sat. aq. NaHCO3 solution
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-5cb8898cc5a34cbf8a56570c6ee7e274
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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