Boron trifluoride etherate → HCID 21449337, compound

HRID 597066Notes

Reaction equation

HRID 597066 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[C:20]4[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=4)[C:14]([CH2:23][C:24]([OH:26])=[O:25])=[C:13]3[CH3:27])=[N:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.B(F)(F)F.[CH3:32]COCC.C([O-])(=O)C.[Na+]>CO>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[C:20]4[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=4)[C:14]([CH2:23][C:24]([O:26][CH3:32])=[O:25])=[C:13]3[CH3:27])=[N:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 517045Sodium AcetateHCID 101940031-(7-Chloroquinazolin-4-yl)-5-methoxy-2-methylindol-3-ylacetic acid

Product 1

HCID 21449337HCID 21449337, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(7-chloroquinazolin-4-yl)-5-methoxy-2-methylindol-3-ylacetic acid (1.0g.) in dry methanol (50ml.) was added freshly distilled boron trifluoride etherate (0.5ml.), and the dark red solution was heated under reflux for 30 mins. To the solution was added saturated sodium acetate solution (5ml.), and the mixture was concentrated in vacuo. The residual mixture was shaken with a mixture of water (50ml.) and chloroform (30ml.). The aqueous layer was separated and extracted with further chloroform (2 × 20 ml.), and the combined extracts were washed successively with saturated sodium hydrogen carbonate solution (2 × 20ml.), water (10ml.) and saturated sodium chloride solution (15ml.). After drying, the extracts were evaporated to give methyl 1(7-chloroquinazolin-4-yl)-5-methoxy-2-methylindol-3-ylacetate, m.p. 111°-113° C.

Workup

  1. temperaturethe dark red solution was heated
  2. temperatureunder reflux for 30 mins
  3. concentrationthe mixture was concentrated in vacuo
  4. customThe aqueous layer was separated
  5. extractionextracted with further chloroform (2 × 20 ml.)
  6. washthe combined extracts were washed successively with saturated sodium hydrogen carbonate solution (2 × 20ml.), water (10ml.) and saturated sodium chloride solution (15ml.)
  7. customAfter drying
  8. customthe extracts were evaporated

Sources & evidence

ORD record
ord-584902398f454e8d96826209bbb86b6d
Source dataset
uspto-grants-1977_03
Patent number
US04012513

Reaction notes

Loading…