Triphenylphosphine → 1-(4-((1,5-Naphthyridin-2-yl)methoxy)phenyl)-2-(pyridin-4-yl)ethanone

HRID 2280259ノート

反応式

HRID 2280259 の反応式
[N:1]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][OH:12].O[C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:28])[CH2:21][C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>O1CCOCC1.C(=O)(O)[O-].[Na+]>[N:1]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:14]1[CH:15]=[CH:16][C:17]([C:20](=[O:28])[CH2:21][C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)=[CH:18][CH:19]=1

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 227070041-(4-Hydroxyphenyl)-2-(pyridin-4-yl)ethanoneHCID 67305210HCID 67305210、化合物

生成物 1

HCID 867060331-(4-((1,5-Naphthyridin-2-yl)methoxy)phenyl)-2-(pyridin-4-yl)ethanone収率 39.8%

試薬・触媒・溶媒 2

HCID 312751,4-Dioxane溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

Intermediate 4C, (1,5-naphthyridin-2-yl)methanol (142 mg, 0.887 mmol), Intermediate 4A, 1-(4-hydroxyphenyl)-2-(pyridin-4-yl)ethanone (158 mg, 0.739 mmol), and triphenylphosphine (310 mg, 1.182 mmol) were dissolved in dioxane (6 mL). To this stirred solution was added di-tert-butyl azodicarboxylate (272 mg, 1.182 mmol). The reaction mixture was stirred overnight at ambient temperature under a dry nitrogen atmosphere. The reaction mixture was diluted with aqueous sodium bicarbonate and extracted with CHCl3. The combined organic layers were dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure to give a yellow oil. The oil was purified by column chromatography on an Analogix IF-280 (Varian SF25-80 g, 100% DCM to 97:3 DCM/2M NH3 in MeOH). Fractions #10-22 were combined and concentrated under reduced pressure to give 1-(4-((1,5-naphthyridin-2-yl)methoxy)phenyl)-2-(pyridin-4-yl)ethanone as a pale green solid (104.5 mg, 39.8%). 1H NMR (300 MHz, CDCl3) δ 9.00 (dd, J=4.2, 1.6 Hz, 1H), 8.55 (dd, J=4.5, 1.6 Hz, 2H), 8.48-8.43 (m, 1H), 8.39 (ddd, J=8.5, 1.6, 0.9 Hz, 1H), 8.01-7.95 (m, 2H), 7.90-7.86 (m, 1H), 7.68 (dd, J=4.5, 1.5 Hz, 2H), 7.12-7.06 (m, 2H), 5.47 (s, 2H), 4.22 (s, 2H). MS (DCI—NH3) m/z=356 (M+H)+.

後処理

  1. extractionextracted with CHCl3
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto give a yellow oil
  6. customThe oil was purified by column chromatography on an Analogix IF-280 (Varian SF25-80 g, 100% DCM to 97:3 DCM/2M NH3 in MeOH)
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-27b8dc6e32484071948d468fbb8b15f1
出典データセット
uspto-grants-2015_09
特許番号
US09138494B2

反応ノート

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