Potassium Iodide → HCID 15104472、化合物

HRID 1198295ノート

反応式

HRID 1198295 の反応式
N1C2C(=CC(C(OCC3C=CC=CC=3)=O)=CC=2)C=C1.Br[CH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][C:23]=1[O:32][CH3:33].[I-:34].[K+]>CN(C)C=O>[I:34][CH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][C:23]=1[O:32][CH3:33]

参加物

5

反応物 3

HCID 4875Potassium IodideHCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoateHCID 10264164Benzyl 1H-indole-5-carboxylate

生成物 1

HCID 15104472HCID 15104472、化合物収率 26.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of benzyl indole-5-carboxylate (86.8 g), methyl 4-bromomethyl-3-methoxybenzoate (89.5 g) and potassium iodide (57.4 g) in N,N-dimethylformamide (900 ml) was heated to 80° C. for 10 hours. The reaction mixture was evaporated and partitioned between diethyl ether and water. The organic layer was separated and washed with water. The aqueous washes were combined and extracted with diethyl ether. The combined organic extract was dried (MgSO4) and evaporated. The residue was purified by flash chromatography, eluting sequentially with 0:1:1, 2:48:50, 4:46:50, 5:45:50, and 10:40:50 ethyl acetate:hexane:methylene chloride, to afford methyl 4-iodomethyl-3-methoxybenzoate (27.8 g), recovered benzyl indole-5-carboxylate (29.6 g), and the crude product as a tan solid (50.6 g). Treatment of the recovered benzyl indole-5-carboxylate (29.6 g) in N,N-dimethylformamide (250 ml) with methyl 4-iodomethyl-3-methoxybenzoate (29.8 g) at 80° C. for 12 hours, followed by evaporation, gave a dark residue, which was dissolved in diethyl ether and washed with water (3 times). The aqueous washes were combined and extracted with diethyl ether. The combined organic extract was dried (MgSO4) and evaporated. The residue was purified by flash chromatography, eluting sequentially with 0:1:1, 2:48:50, 5:45:50, and 10:40:50 ethyl acetate:hexane:methylene chloride, to give further crude product as a tan solid (31.9 g). The combined crude product (82.5 g) was suspended in diethyl ether (400 ml), heated to reflux for 30 min, cooled and filtered to obtain methyl 4-(5-benzyloxycarbonylindol-3-ylmethyl)-3-methoxybenzoate as an ivory solid (46.1 g, 31%); partial NMR (250 MHz, CDCl3): 3.84 (s, 3H, CO2CH3), 3.88 (s, 3H, OCH3), 4.14 (s, 2H, CH2), 5.35 (s, 2H, OCH2), 6.97 (d, 1H, indole-H(2)), 8.15 (br, 1H, NH), 8.37 (s, 1H, indole-H(4)).

後処理

  1. customThe reaction mixture was evaporated
  2. custompartitioned between diethyl ether and water
  3. customThe organic layer was separated
  4. washwashed with water
  5. extractionextracted with diethyl ether
  6. extractionThe combined organic extract
  7. dry with materialwas dried (MgSO4)
  8. customevaporated
  9. customThe residue was purified by flash chromatography
  10. washeluting sequentially with 0:1:1, 2:48:50, 4:46:50, 5:45:50, and 10:40:50 ethyl acetate

出典と根拠

ORDレコード
ord-f4c4f1242ecd47ffa6453f942730200f
出典データセット
uspto-grants-1994_01
特許番号
US05280125

反応ノート

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