Cesium carbonate → HCID 67233992, compound

HRID 1805396Notes

Reaction equation

HRID 1805396 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[C@:8]12[CH2:16][C@H:15]1[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)=[O:4].BrC[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[F:32].[C:33]([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:33][C:29]1[CH:30]=[CH:31][CH:26]=[C:27]([F:32])[CH:28]=1)[C:9](=[O:14])[C@@:8]12[CH2:16][C@@H:15]1[C:17]1[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=1)=[O:4]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 67968alpha-Bromo-o-fluorotolueneHCID 67233699HCID 67233699, compound

Product 1

HCID 67233992HCID 67233992, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(1S,2R) and (1R,2S)-methyl-2-(4-fluorophenyl)-2′-oxospiro[cyclopropane-1,3′-indoline]-5′-carboxylate (500 mg, 1.61 mmol), 1-bromomethyl-2-fluoro-benzene (456 mg, 2.14 mmol) and Cs2CO3 (785 mg, 4.2 mmol) were mixed in anhydrous DMF and stirred at room temperature for 8 hours. HPLC monitored the reaction finished. The solvent was removed under reduced pressure. The residue was purified by flash column chromatography (gradient elution, 15-25% ethyl acetate in petroleum ether) to give title compound as white solid (405 mg, 60%). LC/MS m/e calcd. for C25H19F2NO3 420, observed (M+H)+: 420.5.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was purified by flash column chromatography (gradient elution, 15-25% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-a00e0e6b9c334630a21c3e3b23fd0da0
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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