Dichloromethane → HCID 44233103、化合物

HRID 81462

反応式

HRID 81462 の反応式
[NH2:1][C:2]1[C:3]([C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:10])=[N:4][C:5](Br)=[CH:6][N:7]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C(Cl)Cl.C([O-])(=O)C.[K+].Br[C:44]1[CH:45]=[C:46]([S:50]([NH:53][CH2:54][CH2:55][O:56][CH3:57])(=[O:52])=[O:51])[CH:47]=[CH:48][CH:49]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:44]2[CH:45]=[C:46]([S:50]([NH:53][CH2:54][CH2:55][O:56][CH3:57])(=[O:51])=[O:52])[CH:47]=[CH:48][CH:49]=2)=[N:4][C:3]=1[C:9]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)=[O:10]

参加物

10

反応物 6

HCID 6344Dichloromethane2 回HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 471084603-Bromo-n-(2-methoxyethyl)benzenesulfonamideHCID 86634541(3-Amino-6-bromo-pyrazin-2-yl)-pyridin-3-yl-methanone

生成物 1

HCID 44233103HCID 44233103、化合物

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒2 回HCID 80711,2-Dimethoxyethane溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

A suspension of (3-Amino-6-bromo-pyrazin-2-yl)-pyridin-3-yl-methanone (Intermediate AA) (0.05 g, 0.18 mmol), bis(pinacolato)diboron (0.05 g, 0.19 mmol), Pd(dppf)Cl2.DCM (0.015 g, 0.018 mmol) and potassium acetate (0.03 g, 0.27 mmol) in DME (4 ml) is heated at reflux for 4 hours. Pd(dppf)Cl2.DCM (7 mg, 0.009 mmol), 3-Bromo-N-(2-methoxy-ethyl)-benzenesulfonamide (Intermediate DD) (0.05 g, 0.18 mmol), 2M Na2CO3 (1 ml) and DME (3 ml) are added to the suspension, which is heated at reflux for a further 1 hour. After cooling, the reaction mixture is diluted with EtOAc, washed with water, dried (MgSO4) and filtered through a short pad of Celite® (filter material). The solvent is removed in vacuo, and the residue purified by flash column chromatography (SiO2, iso-hexane/EtOAc) to afford the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-6) δ 9.16 (2H, m), 8.86 (1H, dd), 8.43 (1H, dt), 8.37 (1H, m), 8.23 (3H, m), 7.85 (1H, m), 7.77 (1H, m), 7.66 (1H, ddd), 3.38 (2H, t), 3.22 (3H, s), 3.01 (2H, m). MS m/z 414.01 [M+H]+

後処理

  1. temperatureat reflux for 4 hours
  2. temperatureis heated
  3. temperatureat reflux for a further 1 hour
  4. temperatureAfter cooling
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered through a short pad of Celite® (filter material)
  8. customThe solvent is removed in vacuo
  9. customthe residue purified by flash column chromatography (SiO2, iso-hexane/EtOAc)

出典と根拠

ORDレコード
ord-fef29bc2d2ad4c6db5e5f638c60b5596
出典データセット
uspto-grants-2014_09
特許番号
US08846687B2

関連ノート

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