Ammonia → HCID 15469862, compound

HRID 883658Notes

Reaction equation

HRID 883658 reaction equation
C(OC([O:11][C:12]1[N:13]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[C:14]2[C:19]([CH:20]=1)=[CH:18][C:17]([Cl:21])=[CH:16][CH:15]=2)=O)C1C=CC=CC=1.N.O1CCOCC1>[Cl-].[Na+].O>[Cl:21][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]([C:22]([O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:23])[C:12](=[O:11])[CH2:20]2

Participants

5

Reactant 3

HCID 222AmmoniaHCID 312751,4-DioxaneHCID 15469857HCID 15469857, compound

Product 1

HCID 15469862HCID 15469862, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

Benzyl 2-{[(benzyloxy)carbonyl]oxy}-5-chloro-1H-indole-1-carboxylate, intermediate 37 (5.00 g; 11.47 mmol) was treated with a solution of ammonia in dioxane (25.2 ml; 0.50 M; 12.6 mmol) and stirred overnight. Brine was added and the mixture extracted with ethyl acetate. The organic phase was dried (MgSO4) and removed in vacuo, to give a solid residue which was purified by recrystallisation (ethyl acetate), to give the title compound in 59% yield (HPLC purity 88%). MS (ESI+): 302.1; MS (ESI−): 300.1

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customremoved in vacuo
  4. customto give a solid residue which
  5. customwas purified by recrystallisation (ethyl acetate)

Sources & evidence

ORD record
ord-68da5600ff3745038519ea3814b72090
Source dataset
uspto-grants-2012_08
Patent number
US08236963B2

Reaction notes

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