Methanol → HCID 57991940、化合物

HRID 2075353ノート

反応式

HRID 2075353 の反応式
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[N:5][N:6]=[CH:7]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:31]([O-:34])(=[O:33])C.[K+].[CH3:36]O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[CH:7]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:2]([C:31]([O:34][CH3:36])=[O:33])[C:3]=2[CH:4]=[N:5][N:6]=1

参加物

7

反応物 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 517044Potassium AcetateHCID 136493705-Bromophthalazine

生成物 1

HCID 57991940HCID 57991940、化合物収率 32%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a 140 mL pressure flask was added 5-bromophthaiazine (3.5 g, 17 mmol), palladium (II) acetate (0.98 g, 4.4 mmol), triphenylphosphine (1.3 g, 5.0 mmol), potassium acetate (2.1 g, 21 mmol), MeOH (20 mL) and DMF (20 mL). The flask was sealed and purged with CO (3×). The flask was charged with CO to 40 PSI and stirred at 100° C. 15 hours. The suspension was filtered through Celite, the cake was washed with MeOH, and the filtrate was concentrated. The residue was taken up in DCM and washed with saturated sodium bicarbonate (2×), saturated sodium chloride (2×) and water (2×). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was adsorbed on to a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column, eluting with a gradient of EtOAc in hexane to provide methyl phthalazine-5-carboxylate (1.0 g, 32%). LCMS (M+H) 189.2 calc. for C10H9N2O2 189.1. 1H NMR (400 MHz, CDCl3): δ ppm 4.05 (s, 3H) 8.06 (d, J=8.41 Hz, 1H) 8.51-8.56 (m, 1H) 8.71 (d, 1H) 9.64 (s, 2H).

後処理

  1. customThe flask was sealed
  2. custompurged with CO (3×)
  3. additionThe flask was charged with CO to 40 PSI
  4. custom15 hours
  5. filtrationThe suspension was filtered through Celite
  6. washthe cake was washed with MeOH
  7. concentrationthe filtrate was concentrated
  8. washwashed with saturated sodium bicarbonate (2×), saturated sodium chloride (2×) and water (2×)
  9. dry with materialThe organic layer was dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. custompurified by chromatography through a Redi-Sep pre-packed silica gel column
  13. washeluting with a gradient of EtOAc in hexane

出典と根拠

ORDレコード
ord-02c5ef89ed6e4e2b9d716bc2080fc751
出典データセット
uspto-grants-2011_04
特許番号
US07919504B2

反応ノート

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