N-bromobutanimide → 7-Bromo-1-[2-(tert-butyldimethyl-silanyloxy)-propyl]-1H-indazol-6-ol

HRID 2121875Notes

Reaction equation

HRID 2121875 reaction equation
[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][CH:7]([CH3:19])[CH2:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([OH:18])[CH:16]=2)[CH:11]=[N:10]1)([CH3:4])([CH3:3])[CH3:2].[Br:22]N1C(=O)CCC1=O.S(=O)(O)[O-].[Na+]>C1COCC1>[Br:22][C:16]1[C:15]([OH:18])=[CH:14][CH:13]=[C:12]2[C:17]=1[N:9]([CH2:8][CH:7]([O:6][Si:5]([C:1]([CH3:3])([CH3:4])[CH3:2])([CH3:21])[CH3:20])[CH3:19])[N:10]=[CH:11]2

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 23665763Sodium BisulfiteHCID 135843648HCID 135843648, compound

Product 1

HCID 1358436497-Bromo-1-[2-(tert-butyldimethyl-silanyloxy)-propyl]-1H-indazol-6-olYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Step B (6.00 g, 19.6 mmol) in anhydrous THF (300 mL) at 0° C. was added N-bromosuccinimide (3.49 g, 19.6 mmol) in 10 portions over 20 min. The mixture was poured into a saturated aqueous solution of sodium bisulfite (300 mL) and extracted with EtOAc (3×100 mL). The combined extracts were dried (MgSO4) and evaporated to a residue (6.39 g). Chromatography (silica, 10% EtOAc/hexane) gave a solid (4.95 g, 66%): LC/MS (+APCI) m/z 385, 387 (M+H).

Workup

  1. extractionextracted with EtOAc (3×100 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. customevaporated to a residue (6.39 g)

Sources & evidence

ORD record
ord-506dc2d437f5463f876923b89599cc85
Source dataset
uspto-grants-2004_02
Patent number
US06696476B2

Reaction notes

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