Dimethylformamide → HCID 59425549, compound

HRID 502280Notes

Reaction equation

HRID 502280 reaction equation
[CH:1]([O:4][C:5](=[O:25])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[NH:14][C:15]3[C:20]([C:21]=2[Cl:22])=[CH:19][CH:18]=[C:17]([O:23][CH3:24])[CH:16]=3)=[CH:9][CH:8]=1)([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:33][CH:34]1[CH2:36][CH2:35]1.CN(C=O)C>O>[CH:1]([O:4][C:5](=[O:25])[NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:14]([CH2:33][CH:34]3[CH2:36][CH2:35]3)[C:15]3[C:20]([C:21]=2[Cl:22])=[CH:19][CH:18]=[C:17]([O:23][CH3:24])[CH:16]=3)=[CH:11][CH:12]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 81503BromomethylcyclopropaneHCID 59030440HCID 59030440, compound

Product 1

HCID 59425549HCID 59425549, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of [4-(3-Chloro-6-Methoxy-1H-indol-2-yl)-phenyl]-carbamic acid isopropyl ester (50 mg, 0.14 mmol), Cs2CO3 (95 mg, 0.29 mmol), bromomethylcyclopropane (18 μL, 0.18 mmol), and DMF (200 μL) was stirred at 60° C. for 4 h. The reaction mixture was then stirred at room temperature for 1 h, diluted with H2O and extracted with EtOAc. The organic layer was washed with H2O and brine and then dried, concentrated and purified by silica gel chromatography (7:3 CH2Cl2/hexane) to provide [4-(3-chloro-1-cyclopropylmethyl-6-methoxy-1H-indol-2-yl)-phenyl]-carbamic acid isopropyl ester (19 mg, 33%) as a white solid.

Workup

  1. stirringThe reaction mixture was then stirred at room temperature for 1 h
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with H2O and brine
  4. customdried
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography (7:3 CH2Cl2/hexane)

Sources & evidence

ORD record
ord-a87324aa620d41c1b902361ff4761eb0
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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