Potassium Carbonate → 8-(Benzyloxy)-2-(7-ethylimidazo[1,2-a]pyridin-3-yl)quinoline

HRID 1095739ノート

反応式

HRID 1095739 の反応式
[CH2:1]([C:3]1[CH:8]=[CH:7][N:6]2[CH:9]=[CH:10][N:11]=[C:5]2[CH:4]=1)[CH3:2].[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:29]=1[N:28]=[C:27](Cl)[CH:26]=[CH:25]2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.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>[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:29]=1[N:28]=[C:27]([C:9]1[N:6]3[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][C:5]3=[N:11][CH:10]=1)[CH:26]=[CH:25]2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 181844637-Ethylimidazo[1,2-a]pyridineHCID 220422348-(Benzyloxy)-2-chloroquinoline

生成物 1

HCID 667814498-(Benzyloxy)-2-(7-ethylimidazo[1,2-a]pyridin-3-yl)quinoline収率 112.8%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒2 回

実験手順

A mixture of 7-ethylimidazo[1,2-a]pyridine (1.18 g, 8.06 mmol), 8-benzyloxy-2-chloroquinoline (2.17 g, 8.06 mmol), potassium carbonate (2.23 g, 16.2 mmol), palladium (II) acetate (90.5 mg, 0.40 mmol), tetrakis(triphenylphosphine)palladium (0) (466 mg, 0.40 mmol), 1,4-dioxane (33 ml) and water (0.33 ml) was heated under a nitrogen atmosphere overnight. The reaction mixture was diluted with water, extracted with CH2Cl2 and EtOAc, and the combined organic extracts were dried over Na2SO4, filtered and concentrated to afford the desired product (3.45 g) as a solid. MS APCI (+) m/z 380.2 (M+1) detected.

後処理

  1. temperaturewas heated under a nitrogen atmosphere overnight
  2. extractionextracted with CH2Cl2 and EtOAc
  3. dry with materialthe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-c8670632d03d4a3e83be8ca1536c8b24
出典データセット
uspto-grants-2012_03
特許番号
US08138181B2

反応ノート

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