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

HRID 920935노트

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HRID 920935 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
130 °C

실험 절차

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.

후처리

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출처 및 근거

ORD 기록
ord-27870fcda7434709a718caa504b32e4e
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273068B2

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