Ammonium Chloride → HCID 67085964, compound

HRID 2036707Notes

Reaction equation

HRID 2036707 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([C:13]2[CH:21]=[CH:20][C:19]3[N:18]([CH3:22])[C:17]4[CH2:23][CH:24]5[NH:28][CH:27]([C:16]=4[C:15]=3[C:14]=2[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:26][CH2:25]5)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[Cl-].[NH4+]>CCO.O.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]([S:10]([C:13]2[CH:21]=[CH:20][C:19]3[N:18]([CH3:22])[C:17]4[CH2:23][CH:24]5[NH:28][CH:27]([C:16]=4[C:15]=3[C:14]=2[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:26][CH2:25]5)(=[O:11])=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 67085522HCID 67085522, compound

Product 1

HCID 67085964HCID 67085964, compoundYield 66.5%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of the product of step A (48 mg, 0.09 mmol) in EtOH (2 mL) and water (1 mL) was added iron powder (27 mg, 0.48 mmol) and ammonium chloride (5.7 mg, 0.10 mmol). The mixture was heated at reflux for 3 h, cooled to ambient temperature and filtered through a celite bed. The filtrate was extracted with chloroform and the organic layer dried over sodium sulfate then concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 7:3 hexane/ethyl acetate) to give tert-butyl 2-(3-aminophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (28 mg, 62%) as a pale yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.18 (s, 1H), 7.65 (d, J=7.2 Hz, 1H), 7.29 (d, J=8.7 Hz, 2H), 7.17-7.23 (m, 2H), 6.74 (dd, J=7.3, 1.2 Hz, 1H), 5.17-5.36 (m, 1H), 4.57-4.88 (m, 1H), 3.85 (s, 2H), 3.60 (s, 3H), 3.28-3.40 (m, 1H), 2.48 (d, J=16.5 Hz, 1H), 2.17-2.33 (m, 2H), 1.91-1.97 (m, 1H), 1.54-1.65 (m, 1H), 1.37 (br s, 9H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 h
  3. filtrationfiltered through a celite bed
  4. extractionThe filtrate was extracted with chloroform
  5. dry with materialthe organic layer dried over sodium sulfate
  6. concentrationthen concentrated in vacuo
  7. customThe residue was purified by flash column chromatography (SiO2, 7:3 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-faabc213eca44441be336bf36dba89db
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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