Cesium carbonate → HCID 59344924, compound

HRID 18161Notes

Reaction equation

HRID 18161 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[N:12]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:13]2[C:18]([CH:19]=1)=[C:17](Br)[CH:16]=[CH:15][CH:14]=2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:8][C:9]([C:11]1[N:12]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:13]2[C:18]([CH:19]=1)=[C:17]([N:32]1[CH2:33][CH2:34][N:29]([CH3:28])[CH2:30][CH2:31]1)[CH:16]=[CH:15][CH:14]=2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 531671-MethylpiperazineHCID 59344899HCID 59344899, compound

Product 1

HCID 59344924HCID 59344924, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 1-Benzyl-4-bromo-1H-indole-2-carboxylic acid benzyl ester (235 mg, 0.56 mmol) and 1-methyl-piperazine (80 ul, 0.72 mmol) in 5 ml Dioxane was added to a mixture of Pd2(dba)3 (10 mg, 0.01 mmol), BINAP (18 mg, 0.03 mmol), Cs2CO3 (547 mg, 1.68 mmol). With stirring, the solution was heated at 100° C. overnight and was allowed to cool to room temperature. The reaction mixture was filtered through celite and washed with ethyl acetate. The filtrate was concentrated in vacuo and the resulting brown residue was purified by preparative TLC (7% MeOH in CH2Cl2 containing 0.7% NH4OH) to give 174 mg of 1-benzyl-4-(4-methyl-piperazin-1-yl)-1H-indole-2-carboxylic acid benzyl ester as a yellow solid (71%). MS: (M+H)+ 440.3.

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe reaction mixture was filtered through celite
  3. washwashed with ethyl acetate
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe resulting brown residue was purified by preparative TLC (7% MeOH in CH2Cl2 containing 0.7% NH4OH)

Sources & evidence

ORD record
ord-1bd807227f95437ea87419cd4f881686
Source dataset
uspto-grants-2010_06
Patent number
US07741326B2

Reaction notes

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