Stannous chloride dihydrate → HCID 64253229, compound

HRID 571214Notes

Reaction equation

HRID 571214 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[CH2:13][C:14]([O:16][CH3:17])=[O:15])([O-])=O.O.O.[Sn](Cl)Cl.C([O-])(O)=O.[Na+]>C1COCC1>[NH2:1][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[CH2:13][C:14]([O:16][CH3:17])=[O:15]

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 64252249HCID 64252249, compound

Product 1

HCID 64253229HCID 64253229, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of crude methyl 2-(4-nitro-1H-indol-1-yl)acetate (obtained as reported in Example 15, Step 1, theoretical amount 3.08 mmol) in THF (15 ml), tin(II) chloride dihydrate (6.243 g, 27.7 mmol) was added, and the mixture was reacted at 50° C. for 5 hours and at room temperature overnight. A saturated solution of NaHCO3 (120 ml) was added to the cooled reaction mixture, and the resulting precipitate was filtered off on a celite pad. The filtrate was extracted with ethyl acetate (3×20 ml) and the combined organic layers were dried over sodium sulfate. After evaporation of the solvent, crude methyl 2-(4-amino-1H-indol-1-yl)acetate was obtained and used in the next step without any additional purification (810 mg). MS/ESI+ 205.0 [MH]+.

Workup

  1. customthe mixture was reacted at 50° C. for 5 hours and at room temperature overnight
  2. filtrationthe resulting precipitate was filtered off on a celite pad
  3. extractionThe filtrate was extracted with ethyl acetate (3×20 ml)
  4. dry with materialthe combined organic layers were dried over sodium sulfate
  5. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-3b06ca8326624e969ae986819b339a90
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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