Water → HCID 66984843, compound

HRID 1009665Notes

Reaction equation

HRID 1009665 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([OH:12])=[CH:9][CH:10]=2)[N:5]([CH:13]2[CH2:16][CH2:15][CH2:14]2)[C:4]=1[C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:26][S:27]([CH:30]([CH3:32])[CH3:31])(=[O:29])=[O:28])=[O:25])=[CH:19][CH:18]=1)#[N:2].C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:40]1[N:45]=[CH:44][CH:43]=[CH:42][N:41]=1.O>CN(C=O)C>[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([O:12][C:40]3[N:45]=[CH:44][CH:43]=[CH:42][N:41]=3)=[CH:9][CH:10]=2)[N:5]([CH:13]2[CH2:14][CH2:15][CH2:16]2)[C:4]=1[C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:26][S:27]([CH:30]([CH3:32])[CH3:31])(=[O:29])=[O:28])=[O:25])=[CH:19][CH:18]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 744042-ChloropyrimidineHCID 66984574HCID 66984574, compound

Product 1

HCID 66984843HCID 66984843, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-[4-(3-cyano-1-cyclobutyl-6-hydroxy-1H-indol-2-yl)-phenyl]-3-isopropylsulfonylurea (0.085 g, 0.2 mmol), Cs2CO3 (0.163 g, 0.5 mmol), 2-chloropyrimidine (0.034 g, 0.3 mmol) in DMF (2.0 mL) was stirred at 70° C. overnight. After cooling to room temperature the mixture was poured into water (15 mL) and the precipitate collected via filtration, washed with water and purified on silica gel (CH2Cl2/EtOAc, 8.5:1.5) to provide 1-{4-[3-cyano-1-cyclobutyl-6-(pyrimidin-2-yloxy)-1H-indol-2-yl]-phenyl}-3-isopropylsulfonylurea (0.061 g, 61%).

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. filtrationthe precipitate collected via filtration
  3. washwashed with water
  4. custompurified on silica gel (CH2Cl2/EtOAc, 8.5:1.5)

Sources & evidence

ORD record
ord-667a5e070fb749b8ad5588c7dbe9a138
Source dataset
uspto-grants-2011_07
Patent number
US07973069B2

Reaction notes

Loading…