Ethanol → HCID 44596115, compound

HRID 2306978Notes

Reaction equation

HRID 2306978 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[C:11](Cl)([C:13](Cl)=[O:14])=[O:12].[CH3:17][CH2:18][OH:19].C([O-])(O)=O.[Na+]>C1COCC1>[CH2:18]([O:19][C:13](=[O:14])[C:11]([C:6]1[C:5]2[C:9](=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)[NH:8][CH:7]=1)=[O:12])[CH3:17]

Participants

6

Reactant 4

HCID 702EthanolHCID 65578Oxalyl chlorideHCID 3512786-FluoroindoleHCID 516892Sodium Bicarbonate

Product 1

HCID 44596115HCID 44596115, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-fluoroindole (1.18 g, 8.56 mmol) in dry THF (65 mL) at 0° C. under argon was added (COCl)2 (0.93 mL, 10.7 mmol). The reaction mixture was stirred at 0° C. for 2 h and at rt for 15 h. The reaction mixture was cooled to 0° C. and EtOH (0.90 mL, 15.5 mmol) was added. The reaction mixture was stirred at rt for 24 h, then poured into cold satd NaHCO3. The mixture was extracted with EtOAc. The combined EtOAc extracts were washed with satd aq NaHCO3 and brine, dried, and evaporated to give the title compound: TLC Rf=0.48 (19:1 CH2Cl2/Me2CO); MS (ESI−) m/z 234.0; 1H NMR (CDCl3, 300 MHz) δ 10.95 (1H), 8.38 (1H), 8.31 (1H), 7.07 (1H), 4.37 (2H), 1.39 (3H).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. stirringThe reaction mixture was stirred at rt for 24 h
  3. extractionThe mixture was extracted with EtOAc
  4. washThe combined EtOAc extracts were washed with satd aq NaHCO3 and brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-ee97f92a6a5f4704a920222670f9d59e
Source dataset
uspto-grants-2004_12
Patent number
US06828314B2

Reaction notes

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