HCID 178488167, compound → HCID 178462268, compound

HRID 2121908Notes

Reaction equation

HRID 2121908 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[C:6]2[CH2:12][C@H:13]([OH:15])[CH3:14]>ClCCl>[OH:15][C@H:13]([CH3:14])[CH2:12][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([OH:2])[CH:4]=2)[NH:8][N:7]=1

Participants

3

Reactant 1

HCID 178488167HCID 178488167, compound

Product 1

HCID 178462268HCID 178462268, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (R)-1-(5-Methoxy-1H-indazol-3-yl)-propan-2-ol (2.31 g, 11.2 mmol) in anhydrous dichloromethane (50 mL) cooled at −78° C. was added a 1 N borontribromide solution in dichloromethane (33.6 mL, 33.6 mmol). After the addition was complete, the mixture was allowed to warm to ambient temperature and stirred for 2 hours. The mixture was cooled (ice bath) and quenched with 20 mL of water. Dichloromethane was evaporated and the residue was mixed with ethyl acetate (100 mL). To this solution potassium carbonate was added in small portions until gas evolution ceased and the pH was about 8. The mixture was extracted with ethyl acetate (3×100 mL) and the combined extracts were dried and evaporated to dryness. Chromatography on silica (gradient, 50% to 90% ethyl acetate in hexane) gave an oil (1.50 g, 70%): LC/MS (+APCI) m/z 193 (M+H).

Workup

  1. additionAfter the addition
  2. temperatureThe mixture was cooled (ice bath)
  3. customquenched with 20 mL of water
  4. customDichloromethane was evaporated
  5. additionthe residue was mixed with ethyl acetate (100 mL)
  6. additionTo this solution potassium carbonate was added in small portions until gas evolution
  7. extractionThe mixture was extracted with ethyl acetate (3×100 mL)
  8. customthe combined extracts were dried
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-57f84316f70e4b6c8510dd652723e98d
Source dataset
uspto-grants-2004_02
Patent number
US06696476B2

Reaction notes

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