Hexamethylditin → 1-[4-(2,2-dimethylpropyl)-1-trityl-1H-imidazol-2-yl]-2-(4-isothiazol-5-ylphenyl)propan-2-ol

HRID 216368

반응식

HRID 216368 반응식
Br[C:2]1[S:6][N:5]=[CH:4][CH:3]=1.Br[C:8]1[CH:13]=[CH:12][C:11]([C:14]([OH:46])([CH3:45])[CH2:15][C:16]2[N:17]([C:26]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:18]=[C:19]([CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])[N:20]=2)=[CH:10][CH:9]=1.C[Sn](C)C.C[Sn](C)C>O1CCOCC1.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:23][C:22]([CH3:25])([CH3:24])[CH2:21][C:19]1[N:20]=[C:16]([CH2:15][C:14]([C:11]2[CH:12]=[CH:13][C:8]([C:2]3[S:6][N:5]=[CH:4][CH:3]=3)=[CH:9][CH:10]=2)([OH:46])[CH3:45])[N:17]([C:26]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:18]=1

참가 물질

7

반응물 3

HCID 6327618HexamethylditinHCID 126311745-Bromo-1,2-thiazoleHCID 591619942-(4-bromophenyl)-1-[4-(2,2-dimethylpropyl)-1-trityl-1H-imidazol-2-yl]propan-2-ol

생성물 1

HCID 686677351-[4-(2,2-dimethylpropyl)-1-trityl-1H-imidazol-2-yl]-2-(4-isothiazol-5-ylphenyl)propan-2-ol

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

Palladium tetrakis(triphenylphosphine) (39 mg, 0.03 mmol) was added to a degassed, ambient temperature solution of 5-bromoisothiazole (55 mg, 0.34 mmol), 2-(4-bromophenyl)-1-[4-(2,2-dimethylpropyl)-1-trityl-1H-imidazol-2-yl]propan-2-ol (200 mg, 0.34 mmol) and hexamethylditin (110 mg, 0.34 mmol) in 1,4-dioxane (15 mL). After stirring at 90° C. for 16 h, the reaction mixture was diluted with water and extracted with ethyl acetate and methylene chloride. The combined organic extracts were concentrated in vacuo. Chromatography over silica eluting with 0-50% ethyl acetate/hexane afforded 1-[4-(2,2-dimethylpropyl)-1-trityl-1H-imidazol-2-yl]-2-(4-isothiazol-5-ylphenyl)propan-2-ol.

후처리

  1. extractionextracted with ethyl acetate and methylene chloride
  2. concentrationThe combined organic extracts were concentrated in vacuo

출처 및 근거

ORD 기록
ord-237fa4327f57447ba8d9f978e23a8761
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193228B2

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