Ammonium Chloride → HCID 178455474, compound

HRID 1873968Notes

Reaction equation

HRID 1873968 reaction equation
[Si:1]([O:18][C:19]1[CH:27]=[C:26]2[C:22]([CH:23]=[N:24][NH:25]2)=[CH:21][CH:20]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[Cl:34]N1C(=O)CCC1=O.[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[Si:1]([O:18][C:19]1[CH:27]=[C:26]2[C:22]([C:23]([Cl:34])=[N:24][NH:25]2)=[CH:21][CH:20]=1)([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 31398ChlorosuccinimideHCID 23665647Potassium tert-butoxideHCID 59370713HCID 59370713, compound

Product 1

HCID 178455474HCID 178455474, compoundYield 58.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Under nitrogen atmosphere, 6-tert-butyldiphenylsilyloxyindazole (29.246 g) which can be prepared according to the method described in Reference example 36, etc. was dissolved in dehydrated THF (200 mL). After cooling to 0° C., potassium tert-butoxide (18.2190 g; manufactured by Kanto Chemical Co., Inc.) and N-chlorosuccinimide (17.0497 g; manufactured by Kanto Chemical Co., Inc.) were added and then stirred for four hours while increasing the temperature from 0° C. to room temperature. The reaction solution was added to a saturated aqueous solution of ammonium chloride and extraction was carried out twice with ethyl acetate. The organic layer was washed once with brine and dried over magnesium sulfate. After the solvent was evaporated under reduced pressure, the resulting residue was purified by column chromatography (“COLUMN-A”; n-hexane:ethyl acetate=88:12→67:33) to obtain the title compound (18.592 g).

Workup

  1. temperaturewhile increasing the temperature from 0° C. to room temperature
  2. washThe organic layer was washed once with brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter the solvent was evaporated under reduced pressure
  5. customthe resulting residue was purified by column chromatography (“COLUMN-A”; n-hexane:ethyl acetate=88:12→67:33)

Sources & evidence

ORD record
ord-b82e9bc6b7b8403c88c50dabd64c517e
Source dataset
uspto-grants-2012_11
Patent number
US08304443B2

Reaction notes

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