Benzyl Bromide → HCID 86723588、化合物

HRID 918916ノート

反応式

HRID 918916 の反応式
[I:1][C:2]1[C:11]2[C:6](=[CH:7][N:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[NH:4][CH:3]=1.[H-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[NH4+].[Cl-]>CN(C=O)C.O>[CH2:15]([N:4]1[CH:3]=[C:2]([I:1])[C:11]2[C:6](=[CH:7][N:8]=[CH:9][CH:10]=2)[C:5]1=[O:12])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

7

反応物 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 666317994-Iodo-2,7-naphthyridin-1(2H)-one

生成物 1

HCID 86723588HCID 86723588、化合物収率 75%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a solution of 4-iodo-2,7-naphthyridin-1(2H)-one (0.544 g, 2.0 mmol) in anhydrous DMF (10 mL) was added sodium hydride (60% dispersion in mineral oil, 0.104 g, 2.6 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 30 min and then benzyl bromide (0.410 g, 2.4 mmol) was added slowly. The reaction was stirred at 0° C. for 2 h, then allowed to warm to rt and stirred for 17 h. Saturated NH4Cl solution (5 mL) and water (5 mL) were added and the mixture was extracted with ethyl acetate (2×25 mL). The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The product was purified by flash column chromatography (silica gel, 99:1 dichloromethane/methanol to 97:3 dichloromethane/methanol) to give 2-benzyl-4-iodo-2,7-naphthyridin-1(2H)-one (0.540 g, 75%) as an off-white solid: 1H NMR (400 MHz, CDCl3) δ 9.56 (s, 1H), 8.84 (d, J=5.5 Hz, 1H), 7.68 (s, 1H), 7.45 (d, J=5.5 Hz, 1H), 7.30-7.41 (m, 5H), 5.19 (s, 2H); ESI MS m/z 363 [M+H]+.

後処理

  1. stirringThe reaction was stirred at 0° C. for 2 h
  2. temperatureto warm to rt
  3. stirringstirred for 17 h
  4. extractionthe mixture was extracted with ethyl acetate (2×25 mL)
  5. washThe organic phase was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe product was purified by flash column chromatography (silica gel, 99:1 dichloromethane/methanol to 97:3 dichloromethane/methanol)

出典と根拠

ORDレコード
ord-54940f8eed2540039d47782df07a5ae1
出典データセット
uspto-grants-2016_03
特許番号
US09271978B2

反応ノート

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