Water → HCID 66998094, compound

HRID 559162Notes

Reaction equation

HRID 559162 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:29](=[O:30])[N:28]([CH3:31])[C:12]2[N:13]([CH3:27])[C:14]3[C:19]([C:11]=2[CH:10]=1)=[CH:18][C:17]([C:20]1[N:21]=[C:22](CO)[S:23][CH:24]=1)=[CH:16][CH:15]=3.[H-].[Na+].C1(Br)CC1.O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:29](=[O:30])[N:28]([CH3:31])[C:12]2[N:13]([CH3:27])[C:14]3[C:19]([C:11]=2[CH:10]=1)=[CH:18][C:17]([C:20]1[N:21]=[CH:22][S:23][CH:24]=1)=[CH:16][CH:15]=3

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 78037BromocyclopropaneHCID 66998274HCID 66998274, compound

Product 1

HCID 66998094HCID 66998094, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

150 mg (0.3 mmol) of compound 3-(2,4-dichlorophenyl)-6-[2-(hydroxymethyl)-1,3-thiazol-4-yl]-1,9-dimethyl-1,9-dihydro-2H-pyrido[2,3-b]indol-2-one from Example 9 above are dissolved in 10 ml of DMF. 50 mg of 60% NaH (0.96 mmol) are added and the mixture is stirred at ambient temperature for 30 min. 0.05 ml (0.6 mmol) of cyclopropyl bromide are added and the mixture is then stirred at ambient temperature for 3 hours. Water is added and the mixture is extracted with EtOAc. The product is washed with a saturated NaCl solution followed by adsorption onto silica. Purification is carried out by chromatography on a silica column, elution being carried out with EtOAc.

Workup

  1. stirringthe mixture is then stirred at ambient temperature for 3 hours
  2. extractionthe mixture is extracted with EtOAc
  3. washThe product is washed with a saturated NaCl solution
  4. customPurification
  5. washis carried out by chromatography on a silica column, elution

Sources & evidence

ORD record
ord-acc128894d0c4e5a8344a577b6fc4c01
Source dataset
uspto-grants-2011_11
Patent number
US08063061B2

Reaction notes

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