Hydrochloric Acid → methyl 6-iodo-4H-furo[3,2-b]pyrrole-5-carboxylate

HRID 1363303ノート

反応式

HRID 1363303 の反応式
[O:1]1[C:8]2[CH:7]=[C:6]([C:9]([O:11][CH3:12])=[O:10])[NH:5][C:4]=2[CH:3]=[CH:2]1.[OH-].[K+].[I:15]I.Cl>CN(C=O)C.O>[I:15][C:7]1[C:8]2[O:1][CH:2]=[CH:3][C:4]=2[NH:5][C:6]=1[C:9]([O:11][CH3:12])=[O:10]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 14797Potassium HydroxideHCID 5082263methyl 4H-furo[3,2-b]pyrrole-5-carboxylate

生成物 1

HCID 59648511methyl 6-iodo-4H-furo[3,2-b]pyrrole-5-carboxylate収率 45.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
-10 °C

実験手順

A mixture of methyl 4H-furo[3,2-b]pyrrole-5-carboxylate (5.00 g, 30.3 mmol) and KOH (3.40 g, 60.6 mmol) in DMF (100 mL) was cooled to −10° C. Iodine (7.31 g, 28.8 mmol) in DMF (40 mL) was charged via an addition funnel over 30 min. The resulting mixture was warmed to rt and stirred for additional 12 h. The reaction mixture was poured into water, adjusted with HCl (2 N) to pH 6-7, and extracted with EtOAc. The crude product was purified by flash chromatography (silica gel, 0 to 30% ethyl acetate in hexanes) to give a light tan solid methyl 6-iodo-4H-furo[3,2-b]pyrrole-5-carboxylate (3.85 g, 44% yield). 1H NMR (400 MHz, CDCl3) δ (ppm) 8.98 (br, s, 1H); 7.55 (d, J=2 Hz, 1H); 6.52 (d, J=2 Hz, 1H); 3.91 (s, 3H). MS (m/z 291).

後処理

  1. temperatureThe resulting mixture was warmed to rt
  2. extractionextracted with EtOAc
  3. customThe crude product was purified by flash chromatography (silica gel, 0 to 30% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-f7a3e93f2c2b4f05864f36ba15f1c333
出典データセット
uspto-grants-2011_02
特許番号
US07884124B2

反応ノート

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