Potassium Phosphate, Tribasic → HCID 53372995、化合物

HRID 1400462ノート

反応式

HRID 1400462 の反応式
[CH3:1][N:2]1[CH2:14][CH2:13][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:4]=2[CH2:3]1.N1CCC[C@H]1C(O)=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[CH:32]=[C:33]([C:35]1[CH:36]=[CH:37][C:38]([CH3:41])=[N:39][CH:40]=1)[CH3:34]>CN(C=O)C.[Cu]I>[CH3:1][N:2]1[CH2:14][CH2:13][C:5]2[N:6](/[CH:32]=[C:33](/[C:35]3[CH:40]=[N:39][C:38]([CH3:41])=[CH:37][CH:36]=3)\[CH3:34])[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:4]=2[CH2:3]1

参加物

7

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 974242-methyl-2,3,4,5-tetrahydro-1H-pyrido(4,3-b)indoleHCID 145742L-ProlineHCID 866447585-(2-Bromo-1-methyl-vinyl)-2-methyl-pyridine

生成物 1

HCID 53372995HCID 53372995、化合物

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

実験手順

2-Methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (186 mg, 0.8 mmol) was dissolved in DMF (5 mL). Copper (I) iodide (19 mg, 0.10 mmol), L-proline (23 mg, 0.20 mmol) and potassium phosphate (424 mg, 2 mmol) were added and the reaction mixture was stirred for 10 min. at RT. 5-(1-Bromoprop-1-en-2-yl)-2-methylpyridine (212 mg, 1 mmol) was added dropwise and the reaction mixture was purged with nitrogen. The reaction mixture was heated overnight at 80° C. (prolonged heating in some cases was required). DMF was evaporated under reduced pressure, the residue was diluted with water and the solid was filtered. The solid material was purified by silica gel chromatography (100-200 mesh). The product was further purified by HPLC. 1H NMR (CDCl3, TFA salt) δ (ppm): 9.10 (s, 1H), 8.30 (d, 1H), 7.70 (m, 1H), 7.42 (d, 1H), 7.25 (m, 2H), 7.10 (d, 2H), 4.80 (m, 1H), 4.20 (m, 1H), 3.90 (m, 1H), 3.40 (m, 2H), 3.10 (s, 3H), 3.0 (m, 1H), 2.82 (s, 3H), 2.05 (s, 3H).

後処理

  1. customthe reaction mixture was purged with nitrogen
  2. temperatureThe reaction mixture was heated overnight at 80° C. (
  3. temperatureprolonged heating in some cases
  4. customDMF was evaporated under reduced pressure
  5. additionthe residue was diluted with water
  6. filtrationthe solid was filtered
  7. customThe solid material was purified by silica gel chromatography (100-200 mesh)
  8. customThe product was further purified by HPLC

出典と根拠

ORDレコード
ord-06bf65843a64456b9926c8223093447d
出典データセット
uspto-grants-2014_12
特許番号
US08906925B2

反応ノート

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