HCID 58542153, compound → HCID 136197463, compound

HRID 237426Notes

Reaction equation

HRID 237426 reaction equation
C[O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[N:6][N:7]2[C:12]1[CH:17]=[CH:16][N:15]=[C:14]([S:18][CH2:19][CH2:20][CH3:21])[N:13]=1>C(Cl)Cl>[CH2:19]([S:18][C:14]1[N:13]=[C:12]([N:7]2[C:8]3[CH:9]=[CH:10][CH:11]=[C:3]([OH:2])[C:4]=3[CH:5]=[N:6]2)[CH:17]=[CH:16][N:15]=1)[CH2:20][CH3:21]

Participants

3

Reactant 1

HCID 58542153HCID 58542153, compound

Product 1

HCID 136197463HCID 136197463, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

4-Methoxy-1-(2-propylsulfanyl-pyrimidin-4-yl)-1H-indazole was dissolved in methylene chloride (100 mL), and the mixture was cooled to −78° C. and stirred. BBR3 (152.62 uL) was added, and the mixture was allowed to stir overnight at room temperature. The mixture was partitioned between water and methylene chloride, and the combined organic layers were washed with water, saturated aqueous NaHCO3 and brine, dried (MgSO4), filtered and concentrated under reduced pressure to give 1-(2-propylsulfanyl-pyrimidin-4-yl)-1H-indazol-4-ol.

Workup

  1. additionBBR3 (152.62 uL) was added
  2. stirringto stir overnight at room temperature
  3. customThe mixture was partitioned between water and methylene chloride
  4. washthe combined organic layers were washed with water, saturated aqueous NaHCO3 and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5ed618e48f8e44448aac3e2ce5feb467
Source dataset
uspto-grants-2014_02
Patent number
US08642601B2

Reaction notes

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