Tributyl borate → HCID 68466493, compound

HRID 506798Notes

Reaction equation

HRID 506798 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[N:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=2)[C:10](I)=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[B:22](OCCCC)([O:28]CCCC)[O:23]CCCC.[Li]CCCC>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[N:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=2)[C:10]([B:22]([OH:28])[OH:23])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 12712Tributyl borateHCID 68468945HCID 68468945, compoundHCID 178418339Butyllithium

Product 1

HCID 68466493HCID 68466493, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 16.6 g of 1-t-butyloxycarbonyl-3-iodo-5,6-dimethoxy-1H-pyrrolo[3,2-b]pyridine in 300 cm3 of anhydrous tetrahydrofuran, under an inert atmosphere of argon at a temperature in the region of −100° C., are added dropwise 14.41 cm3 of tributyl borate followed by 41 cm3 of n-BuLi (1.6M in hexane). The reaction medium is stirred at this same temperature for 90 minutes. The cooling bath is removed. The temperature rises to −5° C. 100 g of ice are added, followed by 100 cm3 of water and 300 cm3 of ethyl acetate. After separation of the phases by settling, the organic phase is dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue obtained is purified by chromatography (SiO2, dichloromethane/methanol 98/02 by volume as eluents, argon). The fractions containing the product are concentrated under reduced pressure. 8.32 g of 1-t-butyloxycarbonyl-5,6-dimethoxy-1H-pyrrolo[3,2-b]pyridin-3-boronic acid are thus obtained with the following characteristics:

Workup

  1. customThe cooling bath is removed
  2. customrises to −5° C
  3. addition100 g of ice are added
  4. customAfter separation of the phases
  5. dry with materialthe organic phase is dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue obtained
  9. customis purified by chromatography (SiO2, dichloromethane/methanol 98/02 by volume as eluents, argon)
  10. additionThe fractions containing the product
  11. concentrationare concentrated under reduced pressure

Sources & evidence

ORD record
ord-ee356189e5e24fc185e5f31cce3e7de8
Source dataset
uspto-grants-2010_08
Patent number
US07786114B2

Reaction notes

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