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Cesium carbonate → 6-(4-Chloro-benzoyl)-1-cyclopropylmethyl4-(3-iodo-phenyl)-1H-quinolin-2-one

HRID 1369983
Notes
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Reaction equation

HRID 1369983 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[O:18])[CH:12]=[C:11]3[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([I:25])[CH:20]=2)=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:35][CH:36]1[CH2:38][CH2:37]1>CN(C=O)C.ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH2:35][CH:36]2[CH2:38][CH2:37]2)[C:13](=[O:18])[CH:12]=[C:11]3[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([I:25])[CH:20]=2)=[O:7])=[CH:26][CH:27]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 81503BromomethylcyclopropaneHCID 154896296-(4-Chloro-benzoyl)-4-(3-iodo-phenyl)-1H-quinolin-2-one

Product 1

HCID 185164516-(4-Chloro-benzoyl)-1-cyclopropylmethyl4-(3-iodo-phenyl)-1H-quinolin-2-oneYield 63.2%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-(4-Chloro-benzoyl)-4-(3-iodo-phenyl)-1H-quinolin-2-one (9.68 g, 19.9 mmol), prepared as described in PCT international patent application publication number WO 97/21701 (published Jun. 19, 1997) (3.10 g, 7.87 mmol) in DMF (70 mL) was treated with cesium carbonate (23.1 g, 19.9 mmol) and (bromomethyl)cyclopropane (5.37 g, 39.8 mmol). The reaction mixture was stirred at room temperature for 12 hours, diluted with dichloromethane (75 mL), and washed with 1N HCl (2×50 mL) and brine (100 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo to give a black residue. Purification by flash column chromatography (silica, ethyl acetate:petroleum ether 1:9-3:7) gave 6-(4-Chloro-benzoyl)-1-cyclopropylmethyl-4-(3-iodo-phenyl)-1H-quinolin-2-one (6.79 g, 63%) as a yellow solid.

Workup

  1. washwashed with 1N HCl (2×50 mL) and brine (100 mL)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a black residue
  6. customPurification by flash column chromatography (silica, ethyl acetate:petroleum ether 1:9-3:7)

Sources & evidence

ORD record
ord-d5b15369b0a14c25a1f37112589e4e03
Source dataset
uspto-grants-2003_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06579887B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes