Water → HCID 49758888, compound

HRID 1468979Notes

Reaction equation

HRID 1468979 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.[Li]CCCC.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 1F (24.3 g) in tetrahydrofuran (500 mL) at −78° C. was added 2.5M BuLi (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 thee 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 NaOH (69 mL) was added, followed by 30% 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 residue was purified by flash chromatography, eluting with 5-25% ethyl acetate in hexanes to provide the title compound.

Workup

  1. extractionextracted thee 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 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 residue was purified by flash chromatography
  13. washeluting with 5-25% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-f8a53f1861b2464b996d9f3629c9ab8e
Source dataset
uspto-grants-2015_04
Patent number
US09006247B2

Reaction notes

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