2-Chloromethyl 2-(trimethylsilyl)ethyl ether → 6-Bromo-3-(methylsulfonyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-indazole

HRID 1988908Notes

Reaction equation

HRID 1988908 reaction equation
CC(C)([O-])C.[Na+].[Br:7][C:8]1[CH:16]=[C:15]2[C:11]([C:12]([S:17]([CH3:20])(=[O:19])=[O:18])=[N:13][NH:14]2)=[CH:10][CH:9]=1.[CH3:21][Si:22]([CH3:29])([CH3:28])[CH2:23][CH2:24][O:25][CH2:26]Cl>O1CCCC1>[Br:7][C:8]1[CH:16]=[C:15]2[C:11]([C:12]([S:17]([CH3:20])(=[O:18])=[O:19])=[N:13][N:14]2[CH2:26][O:25][CH2:24][CH2:23][Si:22]([CH3:29])([CH3:28])[CH3:21])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 23676156Sodium t-butoxideHCID 178504855HCID 178504855, compound2×

Product 1

HCID 586564536-Bromo-3-(methylsulfonyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-indazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium tert-butoxide (0.057 g) was added to an ice-cold solution of 6-bromo-3-(methylsulfonyl)-1H-indazole (Intermediate 75) (0.14 g) in tetrahydrofuran (1.5 ml). 2-(Trimethylsilyl)ethoxymethyl chloride (0.11 ml) was then added and the mixture was warmed to room temp. over 1 h. The reaction was quenched using 2M aqueous ammonia (1 ml) and methanol (1 ml) the solvent was evaporated and the aqueous residue was extracted with ethyl acetate. The organic extracts were dried using a hydrophobic filter tube and concentrated under vacuum to give the title compound (0.67 g).

Workup

  1. temperaturethe mixture was warmed to room temp. over 1 h
  2. customThe reaction was quenched
  3. customwas evaporated
  4. extractionthe aqueous residue was extracted with ethyl acetate
  5. customThe organic extracts were dried
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b21f3bb84f4b480181fb8baa8ec74e2d
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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