Water → HCID 18005171, compound

HRID 989216Notes

Reaction equation

HRID 989216 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[CH:6]=[CH:5]2.[C:18]([N:25]1[CH:29]=[CH:28]N=[CH:26]1)(N1C=CN=C1)=[O:19].[CH3:30][O:31][C:32]1[CH:33]=[C:34]2C(=[CH:39][C:40]=1[C:41]([F:44])([F:43])[F:42])NCC2.O>ClCCl.CN(C)C=O>[N:14]1[CH:15]=[CH:16][CH:17]=[C:12]([CH2:11][N:7]2[C:8]3[C:4](=[CH:3][C:2]([NH:1][C:18]([N:25]4[C:26]5[C:34](=[CH:33][C:32]([O:31][CH3:30])=[C:40]([C:41]([F:43])([F:44])[F:42])[CH:39]=5)[CH2:28][CH2:29]4)=[O:19])=[CH:10][CH:9]=3)[CH:5]=[CH:6]2)[CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 112067135-Methoxy-6-(trifluoromethyl)indolineHCID 18005184HCID 18005184, compound

Product 1

HCID 18005171HCID 18005171, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

A solution of aminoindole (D48, 0.40 g, 1.8 mmol) and 1,1′-carbonyldiimidazole (0.30 g, 1.8 mmol) in dichloromethane (40 mL) was stirred at room temperature for 1.75 h, then evaporated. To the residue was added dimethylformamide (DMF, 10 mL) and a solution of 5-methoxy-6-trifluoromethylindoline (D11, 0.39 g, 1.8 mmol) in DMF (5 mL). The mixture was stirred at 110° C. overnight, then poured into water and extracted with dichloromethane. The extract was washed with water, dried and evaporated. The residue was triturated with ether to give a grey solid, which was recrystallised from dichloromethane/methanol to give the title compound (0.15 g, 18%) m.p. 243-6° C.

Workup

  1. customevaporated
  2. additionTo the residue was added dimethylformamide (DMF, 10 mL)
  3. extractionextracted with dichloromethane
  4. washThe extract was washed with water
  5. customdried
  6. customevaporated
  7. customThe residue was triturated with ether
  8. customto give a grey solid, which
  9. customwas recrystallised from dichloromethane/methanol

Sources & evidence

ORD record
ord-ebeba4fb395848619ad393bffa12f94a
Source dataset
uspto-grants-2003_10
Patent number
US06638953B2

Reaction notes

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