Methanol → HCID 67783621, compound

HRID 1647822Notes

Reaction equation

HRID 1647822 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]2[CH:13]=[C:14]([C:17]([C:19]3([NH2:38])[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([O:28]C)[CH:26]=4)[N:21]([C:30]4[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=4)[C:20]3=[O:37])=[O:18])[N:15]=[CH:16][C:5]1=2)(=[O:3])[CH3:2].B(Br)(Br)Br.CO>ClCCl>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]2[CH:13]=[C:14]([C:17]([C:19]3([NH2:38])[C:27]4[C:22](=[CH:23][CH:24]=[C:25]([OH:28])[CH:26]=4)[N:21]([C:30]4[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=4)[C:20]3=[O:37])=[O:18])[N:15]=[CH:16][C:5]1=2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 67783061HCID 67783061, compound

Product 1

HCID 67783621HCID 67783621, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 40 ml of dichloromethane was suspended 1.54 g (3.04 mmole) of 3-{9-acetyl-9H-pyrido[3,4-b]-indol-3-yl-carbonyl}-amino-5-methoxy-1-(4-fluorophenyl)-2-indolinone, and to the suspension was added dropwise under ice cooling a solution of 1.1 ml (4 mole equivalent) of boron tribromide dissolved in 10 ml of dichloromethane. After completion of the dropwise addition, the mixture was stirred for 10 minutes under ice cooling and then stirred at room temperature for 1.5 hours. After completion of the reaction, the reaction mixture was treated with methanol under ice cooling, and then the solvent was removed under reduced pressure. Methanol was added to the residue, and the precipitates were collected by filtration to obtain 1.07 g of a hydrobromide of the title compound as pale yellow crystals. Melting point: 239° to 241° C., IR (Nujol) (cm-1): 1720, 1680, FAB-MS (m/z): 495 (MH+, base)

Workup

  1. additionAfter completion of the dropwise addition
  2. stirringstirred at room temperature for 1.5 hours
  3. customAfter completion of the reaction
  4. customthe solvent was removed under reduced pressure
  5. additionMethanol was added to the residue
  6. filtrationthe precipitates were collected by filtration

Sources & evidence

ORD record
ord-1facdf9def874d6b89e3f561e7821897
Source dataset
uspto-grants-1995_07
Patent number
US05434148

Reaction notes

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