Methanol → HCID 21950033, compound

HRID 2215819Notes

Reaction equation

HRID 2215819 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.[C:14](Cl)(=[O:18])[C:15](Cl)=[O:16].C(Cl)Cl.[CH3:23][O-:24].[Na+].CO>C(OCC)C>[F:13][C:2]([F:1])([F:12])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[C:14](=[O:18])[C:15]([O:24][CH3:23])=[O:16]

Participants

7

Reactant 5

HCID 887MethanolHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 27630755-(trifluoromethyl)-1H-indoleHCID 10942334Sodium Methoxide

Product 1

HCID 21950033HCID 21950033, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5-trifluoromethylindole (2.0 g, 10.8 mmol) in diethyl ether (30 mL) at 4° C. was added a 2.0 M solution of oxalyl chloride in methylene chloride (5.5 mL, 11.0 mmol). The resulting solution was allowed to warm to room temperature. After 90 min, the solution was cooled to −78° C. To this solution was added 25% (w/w) solution of sodium methoxide in methanol (5.0 mL, 21.9 mmol). The resulting solution was allowed to warm to room temperature. After one hour, the solution was filtered to give the title compound (1.24 g, 43%) as a yellow solid. 1H NMR (DMSO-d6) δ 8.66 (m, 1H), 8.45 (s, 1H), 7.78 (m, 1H), 7.60 (m, 1H), 3.89 (s, 3H).

Workup

  1. temperaturethe solution was cooled to −78° C
  2. temperatureto warm to room temperature
  3. waitAfter one hour
  4. filtrationthe solution was filtered

Sources & evidence

ORD record
ord-5bc08e1385094d95a62c4d449881e7f9
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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