Ethanol → 3-(Pyridin-4-yl)thieno[3,2-c]pyridin-4(5H)-one

HRID 920935ノート

反応式

HRID 920935 の反応式
Br[C:2]1[C:6]2[C:7](=[O:11])[NH:8][CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+].[N:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1>C1(C)C=CC=CC=1.CC(=O)OCC.O>[N:21]1[CH:26]=[CH:25][C:24]([C:2]2[C:6]3[C:7](=[O:11])[NH:8][CH:9]=[CH:10][C:5]=3[S:4][CH:3]=2)=[CH:23][CH:22]=1

参加物

8

反応物 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 184507963-Bromothieno[3,2-c]pyridin-4(5H)-one

生成物 1

HCID 866834493-(Pyridin-4-yl)thieno[3,2-c]pyridin-4(5H)-one収率 48.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
130 °C

実験手順

3-Bromothieno[3,2-c]pyridin-4(5H)-one (1000 mg, 4.35 mmol) from Example 202.3 was suspended in 2 mL of toluene and 2 mL of ethanol under argon. Then, an aqueous solution of sodiumcarbonate (691 mg, 6.52 mmol, 2 M) was added. To the suspension, pyridin-4-boronic acid (534 mg, 4.35 mmol) and then tetrakis(triphenyl phosphine)palladium(0) (502 mg, 0.435 mmol) were added. The reaction mixture was heated in a Biotage microwave at 130° C. for 30 min. Water and EA were added. The precipitate formed was collected to give 480 mg of the title compound. The filtrate was acidified with 2 M HCl and extracted with EA (twice). The aqueous phase was basified and extracted three times with EA. The organic phases were combined, washed with HCl, dried (MgSO4) and evaporated to give further 43 mg of the title compound. Total yield: 523 mg (52.4%). LC-MS: 229.1 [M+H]+; Rt: 0.427.

後処理

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出典と根拠

ORDレコード
ord-27870fcda7434709a718caa504b32e4e
出典データセット
uspto-grants-2016_03
特許番号
US09273068B2

反応ノート

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