Diglyme → HCID 86639255, compound

HRID 1896514Notes

Reaction equation

HRID 1896514 reaction equation
[Br:1][C:2]1[C:7]2[NH:8][C:9]3[CH:10]=[CH:11][C:12]([F:15])=[CH:13][C:14]=3[C:6]=2[C:5](Cl)=[N:4][CH:3]=1.CC[N:19]([CH:23]([CH3:25])C)[CH:20]([CH3:22])C.CO[CH2:28][CH2:29][O:30][CH2:31][CH2:32]OC>CCOC(C)=O>[Br:1][C:2]1[C:7]2[NH:8][C:9]3[CH:10]=[CH:11][C:12]([F:15])=[CH:13][C:14]=3[C:6]=2[C:5]([N:19]2[CH2:20][CH2:22][C:31]3([C:32]4[CH:3]=[CH:2][CH:7]=[CH:6][C:28]=4[CH2:29][O:30]3)[CH2:25][CH2:23]2)=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 8150DiglymeHCID 81531DiisopropylethylamineHCID 59198464HCID 59198464, compound

Product 1

HCID 86639255HCID 86639255, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

4-Bromo-1-chloro-8-fluoro-5H-pyrido[4,3-b]indole (150 mg, 0.501 mmol) and 3H-spiro[2-benzofuran-1,4′-piperidinium]chloride (565 mg, 2.504 mmol) were placed in a vial and suspended in diglyme (3 mL) and Hunig's Base (0.875 mL, 5.01 mmol). The reaction mixture was heated to 150° C. for 4 days. The solution was cooled to ambient temperature, diluted with EtOAc and washed with water. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated. The crude residue was purified on silica gel (EtOAc/hexanes gradient elution).

Workup

  1. temperatureThe solution was cooled to ambient temperature
  2. washwashed with water
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified on silica gel (EtOAc/hexanes gradient elution)

Sources & evidence

ORD record
ord-06dbfa85747c4e119d3b569bc016d002
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

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