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

HRID 1363303노트

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HRID 1363303 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

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온도
-10 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f7a3e93f2c2b4f05864f36ba15f1c333
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07884124B2

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