Ammonia → HCID 57474465, compound

HRID 552962Notes

Reaction equation

HRID 552962 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].[F:13][CH:14]1[C:19](=O)[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15]1.N>C(O)(=O)C.OP(O)(O)=O>[F:13][CH:14]1[C:19]([C:7]2[C:6]3[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)[NH:9][CH:8]=2)=[CH:18][CH2:17][NH:16][CH2:15]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 225235-NitroindoleHCID 10560711TERT-BUTYL 3-FLUORO-4-OXOPIPERIDINE-1-CARBOXYLATE

Product 1

HCID 57474465HCID 57474465, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent3×HCID 1004Phosphoric AcidSolvent

Procedure

A solution of 5-nitroindole (38) (1.0 g, 6.167 mmol) in glacial acetic acid (10 mL) at 90° C. was treated with compound 130 (1.33 g, 6.167 mmol) in glacial AcOH (5 mL), 1 M H3PO4 in glacial AcOH (5 mL) and the resulting solution was stirred at same temperature for 16 h. The reaction was brought to room temperature, poured into 15% cold aqueous ammonia solution (100 mL) and product was extracted into ethyl acetate (2 50 mL). The combined ethyl acetate layer was washed with brine (25 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2 M NH3 in methanol: CH2Cl2, 1:99 to 5:95) to obtain compound 131 (0.75 g, 47%) as a yellow solid. mp 205-207° C.; 1H NMR (DMSO-d6) δ 2.35 (brs, 1H), 2.86-3.06 (m, 1H), 3.19-3.26 (m, 1H), 3.35-3.58 (m, 2H), 5.28 (d, 1H, J=49.5 Hz), 6.53-6.56 (m, 1H), 7.58 (d, 1H, J=8.7 Hz), 7.74 (s, 1H), 8.02 (dd, 1H, J=2.4, 9.0 Hz), 8.68 (d, 1H, J=2.4 Hz), 11.94 (s, 1H); ESI-MS m/z (%): 262 (MH+, 100), 233 (50).

Workup

  1. customwas brought to room temperature
  2. extractionwas extracted into ethyl acetate (2 50 mL)
  3. washThe combined ethyl acetate layer was washed with brine (25 mL)
  4. dry with materialdried (Na2SO4)
  5. customSolvent was evaporated
  6. customcrude was purified by column chromatography (2 M NH3 in methanol: CH2Cl2, 1:99 to 5:95)

Sources & evidence

ORD record
ord-14654d81f8b0494793953dcd2faa0189
Source dataset
uspto-grants-2011_05
Patent number
US07951940B2

Reaction notes

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