Ammonium Chloride → tert-butyl 1-[3-(4-chlorophenyl)-2-hydroxypentan-3-yl]-1H-indazol-4-ylcarbamate

HRID 1427229Notes

Reaction equation

HRID 1427229 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:13]2[C:21]3[C:16](=[C:17]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:18]=[CH:19][CH:20]=3)[CH:15]=[N:14]2)([CH2:11][CH3:12])[CH:9]=[O:10])=[CH:4][CH:3]=1.[CH3:30][Mg]Br.[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:13]2[C:21]3[C:16](=[C:17]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:18]=[CH:19][CH:20]=3)[CH:15]=[N:14]2)([CH2:11][CH3:12])[CH:9]([OH:10])[CH3:30])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 86705040tert-butyl 1-[2-(4-chlorophenyl)-1-oxobutan-2-yl]-1H-indazol-4-ylcarbamateHCID 178418573HCID 178418573, compound

Product 1

HCID 68176123tert-butyl 1-[3-(4-chlorophenyl)-2-hydroxypentan-3-yl]-1H-indazol-4-ylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl 1-[2-(4-chlorophenyl)-1-oxobutan-2-yl]-1H-indazol-4-ylcarbamate (2.50 g, 6.05 mmol) in anhydrous THF (50 mL) was added methylmagnesium bromide (2.5 M in ether, 7.3 mL, 18.15 mmol) at 0° C. The mixture was stirred for anther 30 min at 0° C., then saturated NH4Cl (100 mL) was added and the mixture was extracted with EA. The combined organic layers were washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered and the solvent was removed in vacuo to provide the desired product.

Workup

  1. extractionthe mixture was extracted with EA
  2. washThe combined organic layers were washed with brine (50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-db90d99f2dcd46d580dd1696ad6971ec
Source dataset
uspto-grants-2015_01
Patent number
US08933113B2

Reaction notes

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