Ammonium Chloride → Benzyl 3-(2-amino-1-(6-(2-methoxyethoxy)-1H-indol-3-yl)ethyl)-2-fluorophenylcarbamate

HRID 2361335Notes

Reaction equation

HRID 2361335 reaction equation
[F:1][C:2]1[C:7]([CH:8]([C:13]2[C:21]3[C:16](=[CH:17][C:18]([O:22][CH2:23][CH2:24][O:25][CH3:26])=[CH:19][CH:20]=3)[NH:15][CH:14]=2)[CH2:9][N+:10]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[NH:27][C:28](=[O:37])[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[Cl-].[NH4+]>CO.O1CCCC1.[Zn]>[NH2:10][CH2:9][CH:8]([C:7]1[C:2]([F:1])=[C:3]([NH:27][C:28](=[O:37])[O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:4]=[CH:5][CH:6]=1)[C:13]1[C:21]2[C:16](=[CH:17][C:18]([O:22][CH2:23][CH2:24][O:25][CH3:26])=[CH:19][CH:20]=2)[NH:15][CH:14]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 67994845Benzyl 2-fluoro-3-(1-(6-(2-methoxyethoxy)-1H-indol-3-yl)-2-nitroethyl)phenylcarbamate

Product 1

HCID 67995084Benzyl 3-(2-amino-1-(6-(2-methoxyethoxy)-1H-indol-3-yl)ethyl)-2-fluorophenylcarbamateYield 86%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl 2-fluoro-3-(1-(6-(2-methoxyethoxy)-1H-indol-3-yl)-2-nitroethyl)phenylcarbamate (3.75 g, 7.39 mmol) and ammonium chloride (5.93 g, 111 mmol) in methanol (148 mL) and tetrahydrofuran (148 mL) under nitrogen was added zinc (7.25 g, 111 mmol). After 3 hr, the reaction was filtered through a pad of CELITE®, rinsed with EtOAc and MeOH. The filtrate was concentrated in vacuo. Water (40 mL) was added followed by saturated aq. NaHCO3 (to pH ˜11 by litmus paper) and extracted with EtOAc (4×50 mL). The organic layers were combined, washed with brine (40 mL), dried over MgSO4, and concentrated in vacuo to give the desired product (3.523 g, 6.35 mmol, 86% yield) as a light tan solid.

Workup

  1. filtrationthe reaction was filtered through a pad of CELITE®
  2. washrinsed with EtOAc and MeOH
  3. concentrationThe filtrate was concentrated in vacuo
  4. additionWater (40 mL) was added
  5. extractionextracted with EtOAc (4×50 mL)
  6. washwashed with brine (40 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f3d653f42aeb4830878b4e36b5f63f70
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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