Methane → HCID 67164517, compound

HRID 12205

Reaction equation

HRID 12205 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([N+:21]([O-])=O)[C:14]=1[S:15][CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1.[Cl-].[NH4+].C>C(O)C.C(OCC)(=O)C.[Fe]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH2:21])[C:14]=1[S:15][CH2:16][CH2:17][N:18]([CH3:19])[CH3:20])[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1

Participants

7

Reactant 3

HCID 297MethaneHCID 25517Ammonium ChlorideHCID 67166181[2-(6-chloro-8-nitro-9H-beta-carbolin-7-ylsulfanyl)-ethyl]-dimethyl-amine

Product 1

HCID 67164517HCID 67164517, compoundYield 107%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A 50 ml round-bottom flask with a magnetic stirrer was charged with [2-(6-chloro-8-nitro-9H-β-carbolin-7-ylsulfanyl)-ethyl]-dimethyl-amine (106 mg, 0.30 mmol) in 8 ml of anhydrous ethanol. To the resulting orange mixture at RT was added 0.33 M aqueous ammonium chloride (1.95 ml, 0.64 mmol) and iron powder (540 mg, 9.67 mmol). The reaction mixture was heated to 60° C. and stirred vigorously for 20 hr. Next, the mixture was cooled to RT, diluted with ethyl acetate (20 ml) and activated charcoal (ca. 150 mg) was added. The resulting mixture was filtered through a pad of celite and the resulting filtrate concentrated to afford 103 mg of 6-chloro-7-(2-dimethylamino-ethylsulfanyl)-9H-β-carbolin-8-ylamine as a yellow solid. The crude product was used directly in the coupling step.

Workup

  1. temperatureNext, the mixture was cooled to RT
  2. additionwas added
  3. filtrationThe resulting mixture was filtered through a pad of celite
  4. concentrationthe resulting filtrate concentrated

Sources & evidence

ORD record
ord-6cee690533f34e0b838930aeaf183eee
Source dataset
uspto-grants-2010_06
Patent number
US07727985B2

Linked notes

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