18-Crown-6 → HCID 86667083, compound

HRID 882072Notes

Reaction equation

HRID 882072 reaction equation
[Br:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:22])[C:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][C:10]=3[C:5]2=[CH:4][CH:3]=1.C1OCCOCCOCCOCCOCC[O:25]C1.[O-][Mn](=O)(=O)=O.[K+]>C(Cl)Cl>[Br:1][C:2]1[N:7]=[C:6]2[N:8]([CH3:22])[C:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[C:11](=[O:25])[C:10]=3[C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 516875Potassium PermanganateHCID 71551310tert-Butyl 2-bromo-9-methyl-5,7,8,9-tetrahydro-6H-pyrido[3',4':4,5]pyrrolo[2,3-b]pyridine-6-carboxylate

Product 1

HCID 86667083HCID 86667083, compoundYield 176.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 2-bromo-9-methyl-5,7,8,9-tetrahydro-6H-pyrido[3′,4′:4,5]pyrrolo[2,3-b]pyridine-6-carboxylate (732 mg, 2.0 mmol) in CH2Cl2 (20 mL) at room temperature was added 18-crown-6 (53 mg, 0.20 mmol) followed by addition of KMnO4 (474 mg, 3.0 mmol) in small portions over 20 min. The reaction mixture was stirred at room temperature for 17 h, quenched with saturated sodium metabisulfite solution (20 ml) and extracted with CH2Cl2 (3×20 mL). The combined extracts were dried over sodium sulfate, filtered, and concentrated. Flash chromatography (40 g ISCO column, 100:0 to 65:35 hexanes/EtOAc gradient) gave the title compound (134 mg, 18%) as an orange solid: 1H NMR (500 MHz, DMSO-d6) δ 8.30 (d, J=8.1 Hz, 1H), 7.36 (d, J=8.1 Hz, 1H), 4.22 (t, J=6.4 Hz, 2H), 3.80 (s, 3H), 3.05 (t, J=6.4 Hz, 2H), 1.59 (s, 9H); ESI MS m/z 380 [M+H]+.

Workup

  1. customquenched with saturated sodium metabisulfite solution (20 ml)
  2. extractionextracted with CH2Cl2 (3×20 mL)
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8d57c030723b498bb692e0fbffb668d8
Source dataset
uspto-grants-2015_03
Patent number
US08993765B2

Reaction notes

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