Triethylamine → HCID 21186579, 화합물

HRID 1003612노트

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HRID 1003612 반응식
BrC1(Br)C(=O)C2C(=CC(O[Si](C(C)C)(C(C)C)C(C)C)=C(C)C=2)OC1.[CH3:26][C:27]1[C:28]([Br:51])=[C:29]2[C:34](=[CH:35][C:36]=1[O:37][Si:38]([CH:45]([CH3:47])[CH3:46])([CH:42]([CH3:44])[CH3:43])[CH:39]([CH3:41])[CH3:40])[O:33][CH2:32][C:31](Br)(Br)[C:30]2=[O:50].[F:52][C:53]1[CH:58]=[CH:57][C:56]([C:59]2([OH:65])[CH2:64][CH2:63][NH:62][CH2:61][CH2:60]2)=[CH:55][CH:54]=1.C(N(CC)CC)C>C(#N)C>[Br:51][C:28]1[C:27]([CH3:26])=[C:36]([O:37][Si:38]([CH:39]([CH3:41])[CH3:40])([CH:42]([CH3:43])[CH3:44])[CH:45]([CH3:47])[CH3:46])[CH:35]=[C:34]2[C:29]=1[C:30](=[O:50])[C:31]([N:62]1[CH2:61][CH2:60][C:59]([C:56]3[CH:57]=[CH:58][C:53]([F:52])=[CH:54][CH:55]=3)([OH:65])[CH2:64][CH2:63]1)=[CH:32][O:33]2

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 774974-(4-Fluorophenyl)piperidin-4-olHCID 21186588HCID 21186588, 화합물HCID 21186638HCID 21186638, 화합물

생성물 1

HCID 21186579HCID 21186579, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 3,3-dibromo-6-methyl-7-triisopropylsilyloxychroman-4-one and 6-methyl-3,3,5-tribromo-7-triisopropylsilyloxychroman-4-one (the compounds of Preparation 34, 1.0 g), 4-(4-fluorophenyl)-4-hydroxypiperidine (0.79 g, 4.05 mmol) and triethylamine (0.60 mL, 4.30 mmol) in acetonitrile (30 mL) was stirred 30 min at ambient temperature. The precipitate which formed was collected by filtration to afford 0.188 g of 5-bromo-6-methyl-7-triisopropylsilyloxy-3-(4-(4-fluorophenyl)-4-hydroxypiperidin-1-yl)-chromen-4-one. The filtrate was flash chromatographed on silica gel (1×4 inches packed in hexane) with elution proceeding as follows: 20% ethyl acetate/hexane (100 mL), 0.115 g of 6-methyl -7-triisopropylsilyloxy-3-(4-(4-fluorophenyl)-4-hydroxypiperidin-1-yl)-chromen-4-one as a light yellow solid which had mp 193-195° C.; 20% ethyl acetate/hexane (100 mL) and 40% ethyl acetate/hexane (100 mL), 0.07 g of a mixture; 40% ethyl acetate/hexane (100 mL) and 60% ethyl acetate/hexane (400 mL), 0.30 g of 6-methyl-7-hydroxy-3-(4-(4-fluorophenyl)-4-hydroxypiperidin-1-yl)-chromen-4-one.

후처리

  1. customThe precipitate which formed
  2. filtrationwas collected by filtration

출처 및 근거

ORD 기록
ord-e8d388ba44b84355980e51a770b5f8a5
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06046213

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