Pyrrolidine → HCID 69775100, compound

HRID 602796Notes

Reaction equation

HRID 602796 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C:4]([S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24](Br)[CH:23]=1)(=[O:21])=[O:20])([CH:6]1[CH2:18][C:9]2[NH:10][C:11]3[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][C:16]=3[C:8]=2[CH2:7]1)[CH3:5].CC([O-])(C)C.[Na+].[NH:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1.C([O-])(O)=O.[Na+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][O:2][C:3](=[O:29])[C:4]([CH:6]1[CH2:18][C:9]2[NH:10][C:11]3[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][C:16]=3[C:8]=2[CH2:7]1)([S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([N:36]2[CH2:40][CH2:39][CH2:38][CH2:37]2)[CH:23]=1)(=[O:21])=[O:20])[CH3:5]

Participants

7

Reactant 4

HCID 31268PyrrolidineHCID 516892Sodium BicarbonateHCID 23676156Sodium t-butoxideHCID 67266944HCID 67266944, compound

Product 1

HCID 69775100HCID 69775100, compoundYield 35.9%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A solution of 40 mg (0.08 mmol) (RS, SR)-2-(3-bromo-benzenesulfonyl)-2-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-propionic acid methyl ester (example 103) in toluene was treated with 13 mg (0.13 mmol) of NaOtBu, 2 mg (0.007 mmol) of 2-(di-tbutylphosphino)biphenyl, 0.03 mL (0.4 mmol) of pyrrolidine and 4 mg (0.004 mmol) of tris(dibenzylideneacetone)dipalladium. The resulting suspension was stirred at 80° for 4 hrs, treated with a diluted aqueous NaHCO3-solution and extracted twice with EtOAc. The combined organic phases were dried over Na2SO4, filtered and evaporated to give 14 mg (35%) of (RS, SR)-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-2-(3-pyrrolidin-1-yl-benzenesulfonyl)-propionic acid methyl ester as a light brown solid, MS: 488 (MH+).

Workup

  1. extractionextracted twice with EtOAc
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-5b8734af36464bc48406ead164d0c99f
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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