Potassium Carbonate → 8-Bromo-1,2,3,4-tetrahydronapthyridine

HRID 1861683ノート

反応式

HRID 1861683 の反応式
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][N:9]=2)[CH2:4][CH2:3][CH2:2]1.[Br:11]N1C(=O)CCC1=O.C([O-])([O-])=O.[K+].[K+]>C(O)(=O)C>[Br:11][N:9]1[C:10]2[NH:1][CH2:2][CH2:3][CH2:4][C:5]=2[CH:6]=[CH:7][CH2:8]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 130473671,2,3,4-Tetrahydro-1,8-naphthyridine

生成物 1

HCID 865841748-Bromo-1,2,3,4-tetrahydronapthyridine

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a solution of 0.6730 g (5.02 mmol) 32 in 20 mL glacial acetic acid was added 1.0701 g (6.01 mmol) N-bromosuccinimide. After 16 h at 65° C., the reaction mixture was cooled to room temperature and poured onto 50 mL ice water. This was brought to pH 11 with K2CO3 and extracted with 4×100 mL CHCl3. The combined CHCl3 extracts were washed with 100 mL brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (50×115 mm silica gel, linear gradient 2-5% (10% NH4H:MeOH):CH2Cl2) yielded 33. 1H NMR (CDCl3, 400 MHz) δ 8.175 (s, 1H, ArH); 7.877 (s, 1H, ArH); 3.458-3.423 (m, 2H, CH2); 2.725 (t, 2H, J=6.26 Hz, CH2); 1.970-1.911 (m, 2H, CH2); MS (Electrospray): m/z 212.9, 214.8 (M+H, 79Br, 81Br).

後処理

  1. extractionextracted with 4×100 mL CHCl3
  2. washThe combined CHCl3 extracts were washed with 100 mL brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (50×115 mm silica gel, linear gradient 2-5% (10% NH4H:MeOH):CH2Cl2)

出典と根拠

ORDレコード
ord-f0057b796b874921a888db3bf6e4eb38
出典データセット
uspto-grants-2003_03
特許番号
US06534510B2

反応ノート

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