Water → HCID 49758888, compound

HRID 2196769Notes

Reaction equation

HRID 2196769 reaction equation
Br[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[C:5]2=[N:6][CH:7]=1.C([Li])CCC.C[O:27]B(OC)OC.O>O1CCCC1>[CH:12]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[N:8]1[C:5]2=[N:6][CH:7]=[C:2]([OH:27])[CH:3]=[C:4]2[CH:10]=[CH:9]1)([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 8470Trimethyl borateHCID 242292235-Bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridineHCID 178418339Butyllithium

Product 1

HCID 49758888HCID 49758888, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of EXAMPLE 43A (24.3 g) in tetrahydrofuran (500 mL) at −78° C. was added 2.5 M n-butyllithium (30.3 mL). After 2 minutes, trimethylborate (11.5 mL) was added, and the mixture was allowed to warm to room temperature over 1 hour. The reaction was poured into water, extracted three times with ethyl acetate, and the combined extracts were washed with brine and concentrated. The crude product was taken up in tetrahydrofuran (200 mL) at 0° C., and 1M aqueous NaOH (69 mL) was added, followed by 30% aqueous H2O2 (8.43 mL), and the solution was stirred for 1 hour. Na2S2O3 (10 g) was added, and the pH was adjusted to 4-5 with concentrated HCl and solid NaH2PO4. The solution was extracted twice with ethyl acetate, and the combined extracts were washed with brine, dried (Na2SO4), filtered, and concentrated. The crude product was chromatographed on silica gel with 5-25% ethyl acetate/hexanes.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washthe combined extracts were washed with brine
  3. concentrationconcentrated
  4. customwas taken up in tetrahydrofuran (200 mL) at 0° C.
  5. addition1M aqueous NaOH (69 mL) was added
  6. additionNa2S2O3 (10 g) was added
  7. extractionThe solution was extracted twice with ethyl acetate
  8. washthe combined extracts were washed with brine
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe crude product was chromatographed on silica gel with 5-25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-500c64f5640e42d5937f69a48f1deaf4
Source dataset
uspto-grants-2012_12
Patent number
US08338466B2

Reaction notes

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