HCID 22610297, compound → HCID 22610291, compound

HRID 2306853Notes

Reaction equation

HRID 2306853 reaction equation
[CH:1]([C:14]1[C:22]2[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=2)[NH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[CH:29]([S:31]([C:34]1[CH:39]=[CH:38][C:37]([CH2:40][CH2:41][C:42]([O:44]C)=[O:43])=[CH:36][CH:35]=1)(=[O:33])=[O:32])=[CH2:30]>C1COCC1>[CH:1]([C:14]1[C:22]2[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=2)[N:16]([CH2:30][CH2:29][S:31]([C:34]2[CH:39]=[CH:38][C:37]([CH2:40][CH2:41][C:42]([OH:44])=[O:43])=[CH:36][CH:35]=2)(=[O:32])=[O:33])[CH:15]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 22610297HCID 22610297, compoundHCID 22610299HCID 22610299, compoundHCID 178418339Butyllithium

Product 1

HCID 22610291HCID 22610291, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-benzhydryl-6-chloro-1H-indole (1.0 eq) in THF (0.1 M), at −78° C., was added a 2.5 M solution of n-butyllithium (1.0 eq). After 0.5 h, the solution was warmed to room temperature and then treated with methyl 3-[4-(vinylsulfonyl)phenyl]propanoate (1.2 eq). The mixture was stirred for 3 h, quenched with saturated ammonium chloride solution, and extracted with ethyl acetate. The organic solution was washed with saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate, and evaporated. The crude material was chromatographed with silica gel to give the desired product in 84% yield.

Workup

  1. customquenched with saturated ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. washThe organic solution was washed with saturated sodium bicarbonate solution and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe crude material was chromatographed with silica gel

Sources & evidence

ORD record
ord-6ba58c2c796d4ccdb3a54f4883f47e26
Source dataset
uspto-grants-2004_12
Patent number
US06828344B1

Reaction notes

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