Water → 1'-(5-iodo-1H-benzimidazol-2-yl)spiro[isobenzofuran-1,4'-piperidin]-3-one

HRID 496251

반응식

HRID 496251 반응식
Cl[N:2]1[C:6]2[CH:7]=[CH:8][C:9]([I:11])=[CH:10][C:5]=2[N:4]=[CH:3]1.[NH:12]1[CH2:17][CH2:16][C:15]2([C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19](=[O:26])[O:18]2)[CH2:14][CH2:13]1.O>CN1C(=O)CCC1>[I:11][C:9]1[CH:8]=[CH:7][C:6]2[NH:2][C:3]([N:12]3[CH2:17][CH2:16][C:15]4([C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[C:19](=[O:26])[O:18]4)[CH2:14][CH2:13]3)=[N:4][C:5]=2[CH:10]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 98342553H-spiro(isobenzofuran-1,4'-piperidin)-3-oneHCID 22325322chloro-5-iodo-1H-benzimidazole

생성물 1

HCID 1785190321'-(5-iodo-1H-benzimidazol-2-yl)spiro[isobenzofuran-1,4'-piperidin]-3-one

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

Heat a solution of 2 chloro-5-iodo-1H-benzimidazole (3.0 g, 10.7 mmol) and spiro[isobenzofuran-1,4′-piperidin]-3-one (2.63 g, 12.9 mmol) in dry NMP (15 mL) at 100° C. for 14 hours. Pour the cooled mixture into water (50 mL) and extract twice with EtOAc (50 mL). Wash the combined extracts with brine (30 mL), dry, and evaporate in vacuo. Purify by flash column chromatography (50% EtOAc-hexane) to obtain 1′-(5-iodo-1H-benzimidazol-2-yl)-spiro[isobenzofuran-1,4′-piperidin]-3-one as a beige solid. C. 1′-(5-Pyridin-3-yl-1G-benzimidazol-2-yl)-spiro[isobenzofuran-1,44′-piperidin]-3-one

후처리

  1. extractionextract twice with EtOAc (50 mL)
  2. washWash the combined extracts with brine (30 mL)
  3. customdry
  4. customevaporate in vacuo
  5. customPurify by flash column chromatography (50% EtOAc-hexane)

출처 및 근거

ORD 기록
ord-887950b534344fe5a0040ebba87360e7
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06943199B2

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