Triethylamine → HCID 21186579、化合物

HRID 1384308ノート

反応式

HRID 1384308 の反応式
Br[C:2]1(Br)[C:11](=[O:12])[C:10]2[C:5](=[CH:6][C:7](O[Si](C(C)C)(C(C)C)C(C)C)=[C:8](C)[CH:9]=2)O[CH2:3]1.[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]C1C=CC=CC=1C1(O)CCNCC1.[CH2:66]([N:68](CC)CC)[CH3:67]>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:68]1[CH2:3][CH2:2][C:11]([C:10]3[CH:9]=[CH:8][C:7]([F:52])=[CH:6][CH:5]=3)([OH:12])[CH2:67][CH2:66]1)=[CH:32][O:33]2

参加物

6

反応物 4

HCID 8471TriethylamineHCID 51954394-(2-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-ce2d6cbaf95d491daf75585a59c07c00
出典データセット
uspto-grants-2001_07
特許番号
US06258827B1

反応ノート

読み込み中…