3-Butyn-1-OL → HCID 9844719, 화합물

HRID 2299296노트

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HRID 2299296 반응식
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

참가 물질

6

반응물 2

HCID 135663-Butyn-1-OLHCID 9845342HCID 9845342, 화합물

생성물 1

HCID 9844719HCID 9844719, 화합물수율 64%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8021Diethylamine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-83044f2e42084394a50943dc77aaffd3
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06495683B2

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