2-Bromoethanol → HCID 18447090, compound

HRID 1269808Notes

Reaction equation

HRID 1269808 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][N:12]=[CH:11]3)[CH2:3][CH2:2]1.Br[CH2:18][CH2:19][OH:20].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH:13]1[C:14]2[C:10](=[CH:9][C:8]([O:7][CH:4]3[CH2:3][CH2:2][N:1]([CH2:18][CH2:19][OH:20])[CH2:6][CH2:5]3)=[CH:16][CH:15]=2)[CH:11]=[N:12]1

Participants

5

Reactant 3

HCID 108982-Bromoethanol2×HCID 11430Potassium CarbonateHCID 229334675-(piperidin-4-yloxy)-1H-indazole

Product 1

HCID 18447090HCID 18447090, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the 5-(piperidin-4-yloxy)-1H-indazole (31 mg, 0.143 mmol) obtained in Example 42 in N,N-dimethylformamide (1 ml) were added 2-bromoethanol (0.0121 ml, 0.171 mmol) and potassium carbonate (49 mg, 0.357 mmol). After 17 hours, 2-bromoethanol (0.0121 ml, 0.171 mmol) was further added thereto. After another 24 hours, the reaction mixture was filtered by the use of Celite and the filtrate was concentrated under reduced pressure. The resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol→chloroform/methanol/(1%-aqueous ammonia)) to obtain 2-[4-(1H-indazol-5-yloxy)piperidin-1-yl]ethanol (14 mg, 38%).

Workup

  1. waitAfter another 24 hours
  2. filtrationthe reaction mixture was filtered by the use of Celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol→chloroform/methanol/(1%-aqueous ammonia))

Sources & evidence

ORD record
ord-8a30f219c053481e86e91aeedcc34634
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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