Diisopropylethylamine → HCID 68676237, compound

HRID 2109017Notes

Reaction equation

HRID 2109017 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, compound

Product 1

HCID 68676237HCID 68676237, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.36 g of trimethyloxonium tetrafluoroborate are added batchwise to a solution of 3.52 g of 1-acetyl-3-[1-hydroxy-1-(3-iodo-phenyl)-methylene]-6-chloro-2-indolinone (educt VII) and 2.72 ml of ethyldiisopropylamine in 80 ml dichloromethane and the mixture is stirred for one hour at ambient temperature. Then another 1.4 ml ethyldiisopropylamine and 1.2 g trimethyloxonium tetrafluoroborate are added and the mixture is stirred for a further two hours at ambient temperature. Then it is extracted with water, the organic phase is dried over magnesium sulphate and evaporated to dryness. The residue is recrystallised from ether and dried in vacuo at 80° C.

Workup

  1. stirringthe mixture is stirred for a further two hours at ambient temperature
  2. extractionThen it is extracted with water
  3. dry with materialthe organic phase is dried over magnesium sulphate
  4. customevaporated to dryness
  5. customThe residue is recrystallised from ether
  6. customdried in vacuo at 80° C.

Sources & evidence

ORD record
ord-ec0b5c69946949bb867b5cc39ebb2471
Source dataset
uspto-grants-2009_04
Patent number
US07514468B2

Reaction notes

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