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Sodium Carbonate → [3-Amino-6-(1h-indol-5-yl)-pyrazin-2-yl]-pyridin-3-yl-methanone

HRID 81460
ノート
印刷プレビュー

反応式

HRID 81460 の反応式
C1(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH2:31][C:32]1[C:33]([C:39]([C:41]2[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=2)=[O:40])=[N:34][C:35](Br)=[CH:36][N:37]=1.B(O)(O)[C:48]1[NH:56][C:55]2[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=2)[CH:49]=1.C([O-])([O-])=O.[Na+].[Na+]>CCOC(C)=O.C([O-])(O)=O.[Na+].C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl.C(O)C>[NH2:31][C:32]1[C:33]([C:39]([C:41]2[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=2)=[O:40])=[N:34][C:35]([C:52]2[CH:51]=[C:50]3[C:55](=[CH:54][CH:53]=2)[NH:56][CH:48]=[CH:49]3)=[CH:36][N:37]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 10340Sodium CarbonateHCID 821241,4-Bis(diphenylphosphino)butaneHCID 225673581H-Indol-2-ylboronic acidHCID 86634541(3-Amino-6-bromo-pyrazin-2-yl)-pyridin-3-yl-methanone

生成物 1

HCID 44233093[3-Amino-6-(1h-indol-5-yl)-pyrazin-2-yl]-pyridin-3-yl-methanone

試薬・触媒・溶媒 4

HCID 498840
Bis(benzonitrile)palladium chloride
触媒
HCID 702Ethanol溶媒
HCID 8857Ethyl Acetate溶媒
HCID 516892Sodium Bicarbonate溶媒

実験手順

Bis(benzonitrile)palladium(II)chloride (5.2 mg, 0.013 mmol) and 1,4-bis(diphenylphosphino)butane (6.7 mg, 0.015 mmol) in toleune (0.6 ml) are stirred for 20 minutes. (3-Amino-6-bromo-pyrazin-2-yl)-pyridin-3-yl-methanone (Intermediate AA) (0.075 g, 0.27 mmol), 5-indoylboronic acid (0.056 g, 0.35 mmol), ethanol (0.36 ml) and 1M Na2CO3 (0.65 ml) are added and the reaction is heated using microwave radiation at 140° C. for 20 minutes. The mixture is diluted with EtOAc and sat. aq. NaHCO3. The layers are separated and the aqueous layer is extracted with EtOAc. The combined organic extracts are dried (MgSO4), and purified by preperative HPLC (0-100% MeCN in water −0.1% TFA) to yield the title compound as an orange solid. 1H NMR (400 MHz, DMSO-d6) δ11.27 (1H, s), 9.21 (1H, s), 9.09 (1H, s), 8.86 (1H, dd), 8.39-8.41 (1H, dt), 8.19 (1H, s), 7.99 (2H, s), 7.65-7.73 (2H, m), 7.5 (1H, d), 7.44 (1H, t), 6.53 (1H, s). MS ink 316 [M+H]+

後処理

  1. temperaturethe reaction is heated
  2. customat 140° C.
  3. customfor 20 minutes
  4. customThe layers are separated
  5. extractionthe aqueous layer is extracted with EtOAc
  6. dry with materialThe combined organic extracts are dried (MgSO4)
  7. custompurified by preperative HPLC (0-100% MeCN in water −0.1% TFA)

出典と根拠

ORDレコード
ord-70ac452ddcf34943b58bbf6379b1e39b
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08846687B2

反応ノート

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