Triethylamine → HCID 21186579、化合物

HRID 1003612ノート

反応式

HRID 1003612 の反応式
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

参加物

6

反応物 4

HCID 8471TriethylamineHCID 774974-(4-Fluorophenyl)piperidin-4-olHCID 21186588HCID 21186588、化合物HCID 21186638HCID 21186638、化合物

生成物 1

HCID 21186579HCID 21186579、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-e8d388ba44b84355980e51a770b5f8a5
出典データセット
uspto-grants-2000_04
特許番号
US06046213

反応ノート

読み込み中…