Diisopropylethylamine → HCID 68676237, compound

HRID 1985872Notes

Reaction equation

HRID 1985872 reaction equation
F[B-](F)(F)F.[CH3:6][O+](C)C.[C:10]([N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([Cl:22])[CH:20]=2)[C:15](=[C:23]([OH:31])[C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([I:30])[CH:25]=2)[C:14]1=[O:32])(=[O:12])[CH3:11].C(N(C(C)C)C(C)C)C>ClCCl>[C:10]([N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([Cl:22])[CH:20]=2)[C:15](=[C:23]([O:31][CH3:6])[C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([I:30])[CH:25]=2)[C:14]1=[O:32])(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)2×HCID 178473965HCID 178473965, compound2×

Product 1

HCID 68676237HCID 68676237, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A little at a time, 2.36 g of trimethyloxonium tetrafluoroborate are added to a solution of 3.52 g of 1-acetyl-3-[1-hydroxy-1-(3-iodophenyl)methylene]-6-chloro-2-indolinone (starting material VI) and 2.72 ml of ethyldiisopropylamine in 80 ml of dichloromethane, and the mixture is stirred at room temperature for one hour. Another 1.4 ml of ethyldiisopropylamine and 1.2 g of trimethyloxonium tetrafluoroborate are added, and the mixture is stirred at room temperature for another two hours. The mixture is then extracted with water and the organic phase is dried over magnesium sulphate and evaporated to dryness. The residue is recrystallized from ether and dried at 80° C. under reduced pressure.

Workup

  1. stirringthe mixture is stirred at room temperature for another two hours
  2. extractionThe mixture is then extracted with water
  3. dry with materialthe organic phase is dried over magnesium sulphate
  4. customevaporated to dryness
  5. customThe residue is recrystallized from ether
  6. customdried at 80° C. under reduced pressure

Sources & evidence

ORD record
ord-3d37e54f5a6b4a61b524c79633417a41
Source dataset
uspto-grants-2009_06
Patent number
US07547703B2

Reaction notes

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