Dimethylformamide → HCID 66657613, compound

HRID 420925Notes

Reaction equation

HRID 420925 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:15])[CH:13]=2)[N:8]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=2)[C:7]=1[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:5])[CH3:2].Cl[C:34]1[C:43]2[C:38](=[CH:39][C:40]([Cl:44])=[CH:41][CH:42]=2)[N:37]=[CH:36][CH:35]=1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>O>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][C:34]3[C:43]4[C:38](=[CH:39][C:40]([Cl:44])=[CH:41][CH:42]=4)[N:37]=[CH:36][CH:35]=3)[CH:13]=2)[N:8]([C:16]2[CH:17]=[CH:18][C:19]([O:22][C:23]([F:26])([F:24])[F:25])=[CH:20][CH:21]=2)[C:7]=1[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 68664,7-DichloroquinolineHCID 11430Potassium CarbonateHCID 66657846HCID 66657846, compound

Product 1

HCID 66657613HCID 66657613, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 2-ethoxycarbonylmethyl-5-hydroxy-1-(4-trifluoromethoxyphenyl)indole-3-carboxylic acid ethyl ester (100 mg, 0.22 mmol; see step (b) Example 9), 4,7-dichloroquinoline (66 mg, 0.33 mmol), K2CO3 (60 mg, 0.43 mmol) and DMF (2 mL) was stirred at 100-110° C. for 3 h, cooled, diluted with H2O (20 mL) and extracted with Et2O (30 mL). The extract was washed with H2O, dried (Na2SO4, concentrated and purified by chromatography to give the title compound. Yield 48 mg (36%).

Workup

  1. temperaturecooled
  2. extractionextracted with Et2O (30 mL)
  3. washThe extract was washed with H2O
  4. dry with materialdried (Na2SO4
  5. concentrationconcentrated
  6. custompurified by chromatography

Sources & evidence

ORD record
ord-858289a8dff64083b95c6e689c877a34
Source dataset
uspto-grants-2012_01
Patent number
US08097623B2

Reaction notes

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