Ammonium Chloride → Benzyl 3-(2-amino-1-(2-fluorophenyl)ethyl)-1H-indol-6-ylcarbamate

HRID 2361258Notes

Reaction equation

HRID 2361258 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:13]1[C:21]2[C:16](=[CH:17][C:18]([NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:19][CH:20]=2)[NH:15][CH:14]=1)[CH2:9][N+:10]([O-])=O.[Cl-].[NH4+]>O1CCCC1.CO.[Zn]>[NH2:10][CH2:9][CH:8]([C:13]1[C:21]2[C:16](=[CH:17][C:18]([NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[CH:19][CH:20]=2)[NH:15][CH:14]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 67994648Benzyl 3-(1-(2-fluorophenyl)-2-nitroethyl)-1H-indol-6-ylcarbamate

Product 1

HCID 67995367Benzyl 3-(2-amino-1-(2-fluorophenyl)ethyl)-1H-indol-6-ylcarbamateYield 95.5%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of benzyl 3-(1-(2-fluorophenyl)-2-nitroethyl)-1H-indol-6-ylcarbamate (0.600 g, 1.384 mmol), zinc (1.358 g, 20.76 mmol), and ammonium chloride (1.111 g, 20.76 mmol) in tetrahydrofuran (30 mL) and methanol (30.0 mL) was stirred at room temperature for 2 hr. The insoluble material was removed by suction filtration through CELITE®. The filtrate was concentrated under vacuum. The residue was diluted with ethyl acetate (100 mL), washed with 10% NaHCO3 solution (25 mL) and brine (25 mL), and dried over anhydrous MgSO4. Removal of solvent under vacuum provided the desired product (0.586 g, 1.322 mmol, 95% yield) as a pale white solid.

Workup

  1. customThe insoluble material was removed by suction filtration through CELITE®
  2. concentrationThe filtrate was concentrated under vacuum
  3. additionThe residue was diluted with ethyl acetate (100 mL)
  4. washwashed with 10% NaHCO3 solution (25 mL) and brine (25 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. customRemoval of solvent under vacuum

Sources & evidence

ORD record
ord-50e1ad01097241d0be5f687f2982f05a
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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