Cesium fluoride → Dimethyl 3,3'-(1,8-naphthyridine-2,7-diyl)dibenzoate

HRID 1484213ノート

反応式

HRID 1484213 の反応式
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][C:6](Br)=[CH:7][CH:8]=2)[N:3]=1.[CH3:13][O:14][C:15]([C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1)=[O:16].[F-].[Cs+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([C:21]3[CH:22]=[C:17]([CH:18]=[CH:19][CH:20]=3)[C:15]([O:14][CH3:13])=[O:16])[N:5]=2)[CH:10]=[CH:11][C:2]=1[C:21]1[CH:22]=[C:17]([CH:18]=[CH:19][CH:20]=1)[C:15]([O:14][CH3:13])=[O:16]

参加物

5

反応物 3

HCID 25953Cesium fluorideHCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 573521422,7-Dibromo-1,8-naphthyridine

生成物 1

HCID 117940411Dimethyl 3,3'-(1,8-naphthyridine-2,7-diyl)dibenzoate収率 83%

試薬・触媒・溶媒 1

HCID 178418397HCID 178418397、化合物触媒

実験手順

To a 250 mL Schlenk flask, 2,7-dibromo-1,8-naphthyridine (2.00 g, 6.94 mmol), 3-(methoxycarbonyl)phenylboronic acid (3.13 g, 17.40 mmol), CsF (4.00 g), and Pd(PPh3)4 (200 mg) were added. The flask was connected to a Schlenk line and evacuated of air then refilled with nitrogen gas. 130 mL of 1,2-dimethoxyethane (DME) was degassed (two hours) and added to the flask through a canula. The flask was equipped with a water condenser and refluxed under nitrogen gas atmosphere for 3 days. The solvent was removed on rotary evaporator. 100 mL of H2O was added and then extracted with CHCl3. The organic phase was dried with MgSO4. After removal of the CHCl3 solvent, the crude product was purified by column chromatography (silica, ethyl acetate/hexane, 20%) to give a white solid product with a yield of 83% (2.30 g) based on 2,7-dibromo-1,8-naphthyridine. 1H NMR (300 MHz, CD3Cl): δ 3.97 (s, 6H), 7.62 (t, 2H), 8.03 (d, 2H), 8.17 (d, 2H), 8.30 (d, 2H), 8.57 (d, 2H), 8.88 (s, 2H).

後処理

  1. customThe flask was connected to a Schlenk
  2. customline and evacuated of air
  3. additionthen refilled with nitrogen gas
  4. custom130 mL of 1,2-dimethoxyethane (DME) was degassed (two hours)
  5. additionadded to the flask through a canula
  6. customThe flask was equipped with a water condenser
  7. temperaturerefluxed under nitrogen gas atmosphere for 3 days
  8. customThe solvent was removed on rotary evaporator
  9. addition100 mL of H2O was added
  10. extractionextracted with CHCl3
  11. dry with materialThe organic phase was dried with MgSO4
  12. customAfter removal of the CHCl3 solvent
  13. customthe crude product was purified by column chromatography (silica, ethyl acetate/hexane, 20%)
  14. customto give a white solid product with a yield of 83% (2.30 g)

出典と根拠

ORDレコード
ord-9ac69ebd44aa46f699c145cd9ef2d1c8
出典データセット
uspto-grants-2016_08
特許番号
US09421514B2

反応ノート

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