Chloroform → HCID 178518686, compound

HRID 1802508Notes

Reaction equation

HRID 1802508 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[CH:9])[CH:5]=[C:4]([Cl:10])[C:3]=1[NH:11][C:12]1[C:21]2[CH:22]=[CH:23][N:24]=[C:25]([O:26]C)[C:20]=2[C:19]2[C:14](=[CH:15][CH:16]=[N:17][CH:18]=2)[N:13]=1.[Si]([N:32]=[N+:33]=[N-:34])(C)(C)C.C(Cl)(Cl)Cl.B(Br)(Br)Br>C(OCC)(=O)C>[Cl:10][C:4]1[CH:5]=[C:6]([C:8]2[N:32]=[N:33][NH:34][CH:9]=2)[CH:7]=[C:2]([Cl:1])[C:3]=1[NH:11][C:12]1[C:21]2[CH:22]=[CH:23][NH:24][C:25](=[O:26])[C:20]=2[C:19]2[C:14](=[CH:15][CH:16]=[N:17][CH:18]=2)[N:13]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 25134Boron tribromideHCID 78378AzidotrimethylsilaneHCID 59435992HCID 59435992, compound

Product 1

HCID 178518686HCID 178518686, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

N-(2,6-Dichloro-4-ethynylphenyl)-10-methoxypyrido[4,3-c]-1,6-naphthyridin-6-amine (66 mg, 0.167 mmol) and TMS-N3 (1.5 mL, 11.30 mmol) were combined and heated in a sealed tube to 150° C. for 16 h. Volatiles were evaporated under vacuum. To the residue was added chloroform (1 mL) and boron tribromide (1.2 mL, 1.2 mmol, 1M in dichloromethane) and the mixture was heated at 85° C. for 45 min in a sealed tube. After cooling to room temperature, the reaction was diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate, followed by brine. The organic layer was dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was dissolved in THF/MeOH, filtered and purified by reverse phase HPLC to afford the title compound.

Workup

  1. customVolatiles were evaporated under vacuum
  2. temperaturethe mixture was heated at 85° C. for 45 min in a sealed tube
  3. temperatureAfter cooling to room temperature
  4. washwashed with saturated aqueous sodium bicarbonate
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. dissolutionThe residue was dissolved in THF/MeOH
  9. filtrationfiltered
  10. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-1690e5b7bbb0430ea33004d780736e84
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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