Imidazole → 4-Chloro-1-(cyclopropylmethyl)-5-[4-(iodomethyl)cyclohex-1-en-1-yl]-1H-benzotriazole

HRID 1626984노트

반응식

HRID 1626984 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:25]I.[Cl:27][C:28]1[C:36]2[N:35]=[N:34][N:33]([CH2:37][CH:38]3[CH2:40][CH2:39]3)[C:32]=2[CH:31]=[CH:30][C:29]=1[C:41]1[CH2:46][CH2:45][CH:44]([CH2:47]O)[CH2:43][CH:42]=1>O1CCCC1>[Cl:27][C:28]1[C:36]2[N:35]=[N:34][N:33]([CH2:37][CH:38]3[CH2:40][CH2:39]3)[C:32]=2[CH:31]=[CH:30][C:29]=1[C:41]1[CH2:46][CH2:45][CH:44]([CH2:47][I:25])[CH2:43][CH:42]=1

참가 물질

6

반응물 4

HCID 795Imidazole3회HCID 807Iodine3회HCID 11776Triphenylphosphine3회HCID 70977902{4-[4-Chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]cyclohex-3-en-1-yl}methanol

생성물 1

HCID 867137494-Chloro-1-(cyclopropylmethyl)-5-[4-(iodomethyl)cyclohex-1-en-1-yl]-1H-benzotriazole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매4회

실험 절차

To a tetrahydrofuran solution (2 mL) of triphenylphosphine (94 mg, 0.36 mmol, 1.1 equiv) was added imidazole (0.11 g, 1.6 mmol, 5 equiv) and iodine (86 mg, 0.34 mmol, 1.05 equiv). After stirring for 10 minutes, a tetrahydrofuran solution (1.5 mL) of {4-[4-chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]cyclohex-3-en-1-yl}methanol (Example 2, 0.10 g, 0.32 mmol) was added and the mixture was stirred for 1 hour. In a separate flask, a tetrahydrofuran solution (2 mL) was prepared containing triphenylphosphine (94 mg, 0.36 mmol, 1.1 equiv), imidazole (0.11 g, 1.6 mmol, 5 equiv) and iodine (86 mg, 0.34 mmol, 1.05 equiv), which was added to the reaction mixture after stirring for 10 minutes. After stirring for an additional 1 hour, an additional tetrahydrofuran solution (2 mL) containing triphenylphosphine (94 mg, 0.36 mmol, 1.1 equiv), imidazole (0.11 g, 1.6 mmol, 5 equiv) and iodine (86 mg, 0.34 mmol, 1.05 equiv) was added to the reaction mixture. After stirring for an additional 30 minutes, the mixture was purified by silica gel gradient chromatography (100:0 to 0:100; hexanes:ethly acetate), providing the titled compound as a light yellow oil.

후처리

  1. stirringthe mixture was stirred for 1 hour
  2. additionwas added to the reaction mixture
  3. stirringafter stirring for 10 minutes
  4. stirringAfter stirring for an additional 1 hour
  5. additionwas added to the reaction mixture
  6. stirringAfter stirring for an additional 30 minutes
  7. customthe mixture was purified by silica gel gradient chromatography (100:0 to 0:100; hexanes:ethly acetate)

출처 및 근거

ORD 기록
ord-d7995481331540a08c9f82812cacf781
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785482B2

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