Methyl 6-(5-benzyloxy-6-chloro-2-phenylindol-1-ylmethyl)pyridine-2-carboxylate → Methyl 6-(6-chloro-5-hydroxy-2-phenylindol-1-ylmethyl)pyridine-2-carboxylate

HRID 1191666Notes

Reaction equation

HRID 1191666 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[Cl:18])[N:14]([CH2:19][C:20]1[N:25]=[C:24]([C:26]([O:28][CH3:29])=[O:27])[CH:23]=[CH:22][CH:21]=1)[C:13]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[CH:12]2)C1C=CC=CC=1>FC(F)(F)C(O)=O.O.CSC>[Cl:18][C:17]1[CH:16]=[C:15]2[C:11]([CH:12]=[C:13]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:14]2[CH2:19][C:20]2[N:25]=[C:24]([C:26]([O:28][CH3:29])=[O:27])[CH:23]=[CH:22][CH:21]=2)=[CH:10][C:9]=1[OH:8]

Participants

3

Reactant 1

HCID 69670868Methyl 6-(5-benzyloxy-6-chloro-2-phenylindol-1-ylmethyl)pyridine-2-carboxylate

Product 1

HCID 69670789Methyl 6-(6-chloro-5-hydroxy-2-phenylindol-1-ylmethyl)pyridine-2-carboxylateYield 70.4%

Reagents, catalysts & solvents 1

HCID 86597598Trifluoroacetic acid water dimethylsulfideSolvent

Procedure

A solution of methyl 6-(5-benzyloxy-6-chloro-2-phenylindol-1-ylmethyl)pyridine-2-carboxylate (372 mg) in trifluoroacetic acid/water/dimethyl sulfide (95/5/10, 7.7 mL) was stirred at room temperature for 80 hours. The reaction mixture was concentrated under reduced pressure. A saturated aqueous sodium hydrogen carbonate solution (20 mL) was added to the residue and this resulting mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was triturated in dichloromethane/hexane (2/1). The precipitate was collected by filtration, washed with dichloromethane/hexane (2/1), and air-dried to obtain the title compound (213 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionA saturated aqueous sodium hydrogen carbonate solution (20 mL) was added to the residue
  3. extractionthis resulting mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated in dichloromethane/hexane (2/1)
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with dichloromethane/hexane (2/1)
  9. customair-dried

Sources & evidence

ORD record
ord-64cfda7082ed4cbc97f34493cd22c7b8
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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