HCID 86605043, compound → HCID 178519607, compound

HRID 1817488Notes

Reaction equation

HRID 1817488 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1.[CH2:11]([Li])[CH2:12][CH2:13][CH3:14].[C:16]([Li])(C)([CH3:18])[CH3:17].C(O[O:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH:33]=[O:34])C1C=CC=CC=1>CCOCC>[CH2:11]([O:29][C:30]1[CH:31]=[C:32]([CH:33]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[NH:4][N:3]=2)[OH:34])[CH:35]=[CH:36][CH:37]=1)[C:12]1[CH:18]=[CH:16][CH:17]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 86605043HCID 86605043, compoundHCID 178418306HCID 178418306, compoundHCID 178418339ButyllithiumHCID 178419483HCID 178419483, compound

Product 1

HCID 178519607HCID 178519607, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 3-bromoindazole (3.2 g, 16.4 mmol) in 50 mL Et2O was cooled to −78° C. and treated dropwise with n-butyllithium (6.6 mL, 16.4 mmol, 2.5M in hexanes). After the addition was complete, t-butyllithium (19 mL, 32.4 mmol, 1.7M in pentane) was added dropwise to the cooled solution. The mixture was stirred at −78° C. for 15 minutes after which 3-benzyloxyoxybenzaldehyde (3.8 g, 18 mmol) was added in one portion. The cooling bath was removed and the solution was allowed to warm to ambient temperature. The reaction was quenched with 1N HCl and extracted with EtOAc. The organic phase was washed with brine and dried (Na2SO4). Removal of the solvent afforded the crude product which was purified by flash chromatography (silica gel, hexane-ethyl acetate, 3:2) to give the title compound, 1.3 g off-white solid. mp 124-125° C.;

Workup

  1. additionAfter the addition
  2. additionwas added in one portion
  3. customThe cooling bath was removed
  4. customThe reaction was quenched with 1N HCl
  5. extractionextracted with EtOAc
  6. washThe organic phase was washed with brine
  7. dry with materialdried (Na2SO4)
  8. customRemoval of the solvent
  9. customafforded the crude product which
  10. customwas purified by flash chromatography (silica gel, hexane-ethyl acetate, 3:2)

Sources & evidence

ORD record
ord-0469ce9209f14077b00e56b5db721180
Source dataset
uspto-grants-2009_10
Patent number
US07598286B2

Reaction notes

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