Triethylamine → HCID 12018132, compound

HRID 1017559Notes

Reaction equation

HRID 1017559 reaction equation
[C:1](Cl)(=O)[C:2](Cl)=[O:3].[CH3:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1.[CH3:17][C:18]1([CH3:35])[O:22][C@H:21]([CH2:23][O:24][C:25]2[CH:26]=[C:27]([CH2:31][C:32]([OH:34])=[O:33])[CH:28]=[CH:29][CH:30]=2)[CH2:20][O:19]1.CCN(CC)CC>C(OCC)C.ClCCl>[CH3:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:1]2[C:2](=[O:3])[O:33][C:32](=[O:34])[C:31]=2[C:27]2[CH:28]=[CH:29][CH:30]=[C:25]([O:24][CH2:23][C@@H:21]3[CH2:20][O:19][C:18]([CH3:35])([CH3:17])[O:22]3)[CH:26]=2)=[CH:9]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 117811-MethylindoleHCID 65578Oxalyl chlorideHCID 69830595HCID 69830595, compound

Product 1

HCID 12018132HCID 12018132, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Oxalyl chloride (1.05 eq., 4.15 mL) was added dropwise to a solution of N-methylindole (5.8 mL, 50 mmol) in diethyl ether (395 mL) at 0° C. Yellow precipitates were formed. After the completion of the addition, the reaction mixture was stirred at 0° C. for 30 min., and then the volatiles were removed under vacuo. The residue was re-dissolved in dichloromethane (375 mL) and added to a solution of 3-((R)-2,2-dimethyl-1,3-dioxolan-4-ylmethyloxy)phenylacetic acid (13.3 g, 50 mmol) and Et3N (12.5 mL, 2.2eq.) in dichloromethane (375 mL) at 0° C. The resulting mixture was stirred at 0° C. and then allowed to warmed up slowly to room temperature. After stirring overnight, the volatiles were removed and the residue was purified on a silica gel column with dichloromethane to give 3-(1-methylindol-3-yl)-4-{3-((R)-2,2-dimethyl-1,3-dioxolan-4-ylmethyloxy)phenyl]furan-2,5-dione (5.4 g, 27% yield).

Workup

  1. customYellow precipitates
  2. customwere formed
  3. additionAfter the completion of the addition
  4. customthe volatiles were removed under vacuo
  5. dissolutionThe residue was re-dissolved in dichloromethane (375 mL)
  6. stirringThe resulting mixture was stirred at 0° C.
  7. temperatureallowed to warmed up slowly to room temperature
  8. stirringAfter stirring overnight
  9. customthe volatiles were removed
  10. customthe residue was purified on a silica gel column with dichloromethane

Sources & evidence

ORD record
ord-344d6ca010e54d7388d02d106916d994
Source dataset
uspto-grants-2002_11
Patent number
US06479490B2

Reaction notes

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