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1-Propanol → 1-[4-amino-2-ethyl-7-(6-fluoropyridin-3-yl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-ol

HRID 598029
Notes
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Reaction equation

HRID 598029 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][N:3]=1.[NH2:11][C:12]1[C:21]2[N:22]=[C:23]([CH2:30][CH3:31])[N:24]([CH2:25][C:26]([CH3:29])([OH:28])[CH3:27])[C:20]=2[C:19]2[N:18]=[CH:17][C:16](Br)=[CH:15][C:14]=2[N:13]=1.C(O)CC.C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[NH2:11][C:12]1[C:21]2[N:22]=[C:23]([CH2:30][CH3:31])[N:24]([CH2:25][C:26]([CH3:27])([OH:28])[CH3:29])[C:20]=2[C:19]2[N:18]=[CH:17][C:16]([C:5]3[CH:4]=[N:3][C:2]([F:1])=[CH:7][CH:6]=3)=[CH:15][C:14]=2[N:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 10311-PropanolHCID 10340Sodium CarbonateHCID 2783397(6-Fluoropyridin-3-yl)boronic acidHCID 589706911-(4-amino-7-bromo-2-ethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-ol

Product 1

HCID 589706971-[4-amino-2-ethyl-7-(6-fluoropyridin-3-yl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-olYield 73.6%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×

Procedure

2-Fluoropyridine-5-boronic acid (0.468 g, 3.32 mmol) was added to 1-(4-amino-7-bromo-2-ethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-ol (1.1 g, 3.0 mmol) and 1-propanol (10 mL). The mixture was degassed and backfilled with nitrogen. Triphenylphosphine (23.8 mg, 0.0900 mmol), aqueous sodium carbonate (4.53 mL of 2 M), and water (2 mL) were added followed by palladium (II) acetate (6.8 mg, 0.030 mmol). The yellow suspension was heated at reflux for two hours. Water (20 mL) was added, and the 1-propanol was removed under reduced pressure. The remaining mixture was extracted with chloroform (2×100 mL). The combined extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was triturated with acetonitrile and isolated by filtration to provide 0.84 g of 1-[4-amino-2-ethyl-7-(6-fluoropyridin-3-yl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-ol as a white powder, mp 250-251° C.

Workup

  1. customThe mixture was degassed
  2. temperatureThe yellow suspension was heated
  3. temperatureat reflux for two hours
  4. customthe 1-propanol was removed under reduced pressure
  5. extractionThe remaining mixture was extracted with chloroform (2×100 mL)
  6. washThe combined extracts were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product was triturated with acetonitrile
  11. customisolated by filtration

Sources & evidence

ORD record
ord-a51a4eab74e545798ee940f8ed680196
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07897609B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes