Boron trifluoride etherate → 2,2-Dimethyl-propionic acid 5-bromo-3-(1,3-dihydro-isobenzofuran-1-yl)-pyrrolo[2,3-b]pyridin-1-ylmethyl ester

HRID 2234654Notes

Reaction equation

HRID 2234654 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH:11]([OH:20])[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:18]O)=[CH:9][N:8]([CH2:21][O:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[C:5]2=[N:6][CH:7]=1.B(F)(F)F.CCOCC>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH:11]3[C:12]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH2:18][O:20]3)=[CH:9][N:8]([CH2:21][O:22][C:23](=[O:28])[C:24]([CH3:25])([CH3:27])[CH3:26])[C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 68689944HCID 68689944, compound

Product 1

HCID 686916632,2-Dimethyl-propionic acid 5-bromo-3-(1,3-dihydro-isobenzofuran-1-yl)-pyrrolo[2,3-b]pyridin-1-ylmethyl esterYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,2-Dimethyl-propionic acid 5-bromo-3-[hydroxy-(2-hydroxymethyl-phenyl)-methyl]-pyrrolo[2,3-b]pyridin-1-ylmethyl ester (1.60 g, 3.58 mmol) was dissolved in anhydrous dichloromethane (80 ml), and the mixture was stirred at room temperature. Boron trifluoride etherate (374 ul, 2.97 mmol) was added and the mixture stirred for 20 minutes. The reaction was quenched with saturated sodium bicarbonate solution. The organic layer was separated, and the aqueous layer was washed with dichloromethane. The organic layers were combined, dried over magnesium sulfate, and the mixture was concentrated in vacuo. The crude material was purified by flash chromatography (0-100% ethyl acetate in hexanes) to give 1.29 g (84%) of 2,2-dimethyl-propionic acid 5-bromo-3-(1,3-dihydro-isobenzofuran-1-yl)-pyrrolo[2,3-b]pyridin-1-ylmethyl ester. MS: m/z 429.2+431.2 (M+H+).

Workup

  1. stirringthe mixture stirred for 20 minutes
  2. customThe reaction was quenched with saturated sodium bicarbonate solution
  3. customThe organic layer was separated
  4. washthe aqueous layer was washed with dichloromethane
  5. dry with materialdried over magnesium sulfate
  6. concentrationthe mixture was concentrated in vacuo
  7. customThe crude material was purified by flash chromatography (0-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-49732b6d54d2490f94bf8401c6fea045
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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