3-Butyn-1-OL → HCID 9844719、化合物

HRID 2299296ノート

反応式

HRID 2299296 の反応式
Br[C:2]1[S:24][C:5]2[N:6]([CH2:22][CH3:23])[CH:7]=[C:8]([C:11]([NH:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)=[O:12])[C:9](=[O:10])[C:4]=2[CH:3]=1.[CH2:25]([OH:29])[CH2:26][C:27]#[CH:28]>C(NCC)C.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][NH:13][C:11]([C:8]2[C:9](=[O:10])[C:4]3[CH:3]=[C:2]([C:28]#[C:27][CH2:26][CH2:25][OH:29])[S:24][C:5]=3[N:6]([CH2:22][CH3:23])[CH:7]=2)=[O:12])=[CH:16][CH:17]=1

参加物

6

反応物 2

HCID 135663-Butyn-1-OLHCID 9845342HCID 9845342、化合物

生成物 1

HCID 9844719HCID 9844719、化合物収率 64%

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 8021Diethylamine溶媒

実験手順

To a suspension of 2-bromo-N-(4-chlorobenzyl)-7-ethyl4-oxo-4,7-dihydro-thieno[2,3-b]pyridine-5-carboxamide (Example No. 11) (0.500 g) in diethylamine (12 mL) is added copper iodide (0.067 g) and Pd(PPh3)2Cl2 (0.041 g) followed by addition of 3-butyn-1-ol (0.11 mL). The reaction is stirred at rt for 3 d. The diethylamine is removed in vacuo and the resulting residue is partitioned between H2O (50 mL) and CH2Cl2 (50 mL). The organic layer is removed, and the aqueous layer is extracted with CH2Cl2 (3×50 mL). The combined organic layers are washed with a saturated NH4Cl solution (50 mL), dried with MgSO4, filtered, and concentrated in vacuo. The resulting orange solid is purified by column chromatography (CH2Cl2:CH3OH, 98:2). Fractions homogeneous by TLC are combined and concentrated in vacuo. The resulting yellow solid is recrystallized from methanol to yield 0.312 g (64%) of the title compound as a pale yellow, crystalline solid.

後処理

  1. customThe diethylamine is removed in vacuo
  2. customthe resulting residue is partitioned between H2O (50 mL) and CH2Cl2 (50 mL)
  3. customThe organic layer is removed
  4. extractionthe aqueous layer is extracted with CH2Cl2 (3×50 mL)
  5. washThe combined organic layers are washed with a saturated NH4Cl solution (50 mL)
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting orange solid is purified by column chromatography (CH2Cl2:CH3OH, 98:2)
  10. concentrationconcentrated in vacuo
  11. customThe resulting yellow solid is recrystallized from methanol

出典と根拠

ORDレコード
ord-83044f2e42084394a50943dc77aaffd3
出典データセット
uspto-grants-2002_12
特許番号
US06495683B2

反応ノート

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