Potassium methoxide → HCID 56591860, compound

HRID 1629914Notes

Reaction equation

HRID 1629914 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([C:18]2[CH:27]=[CH:26][C:25]([N+]([O-])=O)=[C:24]3[C:19]=2[CH:20]=[CH:21][N:22]=[CH:23]3)[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.[CH3:31][O-:32].[K+]>CO>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([C:18]2[CH:27]=[CH:26][C:25]([O:32][CH3:31])=[C:24]3[C:19]=2[CH:20]=[CH:21][N:22]=[CH:23]3)[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1

Participants

4

Reactant 2

HCID 23664618Potassium methoxideHCID 56591859HCID 56591859, compound

Product 1

HCID 56591860HCID 56591860, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A slurry of 50 mg (0.126 mmol) 2-(2-fluoro-phenyl)-4-(8-nitro-isoquinolin-5-yl)-[1,8]naphthyridine (synthesis see example 6) in 1 ml methanol was treated with 26.5 mg (3.0 mmol) potassium methylate. The mixture was stirred at 60° C. under nitrogen for 18 hours. The reaction mixture was cooled to room temperature. The solid was filtered off, washed with little methanol and dried under vacuum yielding 2-(2-fluoro-phenyl)-4-(8-methoxy-isoquinolin-5-yl)-[1,8]naphthyridine as colourless solid; HPLC/MS: 1.74 min, [M+H] 382.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe solid was filtered off
  3. washwashed with little methanol
  4. customdried under vacuum

Sources & evidence

ORD record
ord-190b032fac8548fabdc1575928c6d134
Source dataset
uspto-grants-2014_07
Patent number
US08791113B2

Reaction notes

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