Water → HCID 178519387, compound

HRID 69194Notes

Reaction equation

HRID 69194 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[CH:5][NH:6][N:7]=2)[CH:3]=1.[Li]CCCC.CN([CH:19]=[O:20])C.O>C1COCC1.CCCCCC>[N:7]1[NH:6][CH:5]=[C:4]2[C:8]=1[CH:9]=[CH:10][C:2]([CH:19]=[O:20])=[CH:3]2

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 178418339ButyllithiumHCID 178419335HCID 178419335, compound

Product 1

HCID 178519387HCID 178519387, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

5-Bromo-2H-indazole (2 g, 9.85 mmol) was dissolved in THF (50 mL) and cooled down to −40° C. n-BuLi in n-hexane (1.6 M, 15.4 mL) was added dropwise. After 15 min stirring, DMF (1.53 mL, 19.7 mmol) was added and the RM was stirred 30 min at −40° C. before warming up to rt. After 1 h, water was added (60 mL) and the mixture was extracted 3 times with EtOAc. Combined organic layers were washed with brine and dried on Na2SO4. After evaporation of the solvent the crude was purified by flash chromatography (CombiFlash® Companion System®, with 12 g RediSep® silica gel column, n-hexane/EtOAc=100:0->50:50) to afford the title compound (tR 3.63 min (conditions 3), MH−=145).

Workup

  1. additionwas added dropwise
  2. stirringthe RM was stirred 30 min at −40° C.
  3. waitAfter 1 h
  4. extractionthe mixture was extracted 3 times with EtOAc
  5. washCombined organic layers were washed with brine
  6. customdried on Na2SO4
  7. customAfter evaporation of the solvent the crude
  8. customwas purified by flash chromatography (CombiFlash® Companion System®, with 12 g RediSep® silica gel column, n-hexane/EtOAc=100:0->50:50)

Sources & evidence

ORD record
ord-5367e676c3e943b29de19014fc77b4be
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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