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Sodium Carbonate → 1-(4-benzylphenyl)-9-(4-hydroxyphenyl)benzo[h][1,6]naphthyridin-2(1H)one

HRID 1944595
ノート
印刷プレビュー

反応式

HRID 1944595 の反応式
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:23]3[C:18](=[CH:19][N:20]=[C:21]4[CH:27]=[CH:26][C:25](Cl)=[CH:24][C:22]4=3)[CH:17]=[CH:16][C:15]2=[O:29])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.C([O-])([O-])=O.[Na+].[Na+].C(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C>O1CCOCC1.CCO.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>[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:23]3[C:18](=[CH:19][N:20]=[C:21]4[CH:27]=[CH:26][C:25]([C:34]5[CH:35]=[CH:36][C:31]([OH:30])=[CH:32][CH:33]=5)=[CH:24][C:22]4=3)[CH:17]=[CH:16][C:15]2=[O:29])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 27343604-Hydroxyphenylboronic acidHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneHCID 585249781-(4-benzylphenyl)-9-chlorobenzo[h][1,6]naphthyridin-2(1H)-one

生成物 1

HCID 461916921-(4-benzylphenyl)-9-(4-hydroxyphenyl)benzo[h][1,6]naphthyridin-2(1H)one収率 64%

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 702Ethanol溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a solution of 1-(4-benzylphenyl)-9-chlorobenzo[h][1,6]naphthyridin-2(1H)-one (100 mg, 0.22 mmol) in 1,4-dioxane (0.6 mL) was added 4-hydroxyphenylboronic acid (45 mg, 0.33 mmol) and 1 N Na2CO3 (0.66 mL, 0.66 mmol). The reaction mixture was degassed using Argon gas for 10 min and added Pd(PPh3)2Cl2 (15 mg, 0.02 mmol) and di-tert-butyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (15 mg, 0.04 mmol). The reaction flask was put into the preheated oil-bath at 100° C. The reaction mixture was further stirred at 100° C. a period of 8 hours after which, it was filtered and partitioned between ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by flash column chromatography using a 97:3 v/v CH2Cl2: EtOH as solvent to afford title compound (64 mg, 64% yield) as a yellow solid. 1H NMR 600 MHz (CDCl3) δ 9.08 (s, 1H), 8.42 (s, 1H), 8.04 (d, J=2.4 Hz, 1H), 7.95 (d, J=8.2 Hz, 1H), 7.61 (dd, J=2.1, 6.6 Hz, 1H), 7.25 (m, 2H), 7.12 (m, 4H), 7.00 (m, 5H), 6.75 (d, J=8.4 Hz, 2H), 6.48 (dd, J=2.4, 6.2 Hz, 1H), 3.88 (s, 2H), MS m/z: 455.27 (M+1).

後処理

  1. customThe reaction mixture was degassed
  2. customfor 10 min
  3. customwas put into the preheated oil-bath at 100° C
  4. filtrationwas filtered
  5. custompartitioned between ethyl acetate and water
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with ethyl acetate
  8. washThe combined organic extracts were washed with brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe crude product was purified by flash column chromatography

出典と根拠

ORDレコード
ord-bc676d62690b4f9385cf7e78f16725e3
出典データセット
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08394818B2

反応ノート

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