Sodium Carbonate → 1-(2-Hydroxyethyl)-5-(4-methylthiophen-2-yl)pyrazin-2(1H)-one

HRID 1878765ノート

反応式

HRID 1878765 の反応式
Br[C:2]1[N:3]=[CH:4][C:5](=[O:11])[N:6]([CH2:8][CH2:9][OH:10])[CH:7]=1.[CH3:12][C:13]1[CH:14]=[C:15](B(O)O)[S:16][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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]>[OH:10][CH2:9][CH2:8][N:6]1[CH:7]=[C:2]([C:15]2[S:16][CH:17]=[C:13]([CH3:12])[CH:14]=2)[N:3]=[CH:4][C:5]1=[O:11]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 27343734-Methylthiophene-2-boronic acidHCID 598431015-Bromo-1-(2-hydroxyethyl)pyrazin-2(1H)-one

生成物 1

HCID 598430841-(2-Hydroxyethyl)-5-(4-methylthiophen-2-yl)pyrazin-2(1H)-one収率 51.4%

試薬・触媒・溶媒 2

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

反応条件

温度
85 °C

実験手順

5-Bromo-1-(2-hydroxyethyl)pyrazin-2(1H)-one (199.6 mg, 911 μmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride (66.6 mg, 91 μmol), and 4-methylthiophen-2-ylboronic acid (253.7 mg, 1787 μmol) were suspended in DME (5.0 mL) and sodium carbonate (1.2 mL, 2.0 M in water, 2.4 mmol) was added. The reaction flask was fit with a reflux condensor and placed in a preheated oil bath (85° C.) and stirred under argon for 1 hour The reaction was then cooled to room temperature and quenched with saturated sodium bicarbonate (5 mL) and allowed to stand at room temperature overnight. It was then extracted with CH2Cl2 and with 10:1 CH2Cl2/MeOH, and the organic extracts were combined, dried over sodium sulfate, filtered, concentrated, and filtered through silica gel (30:1 CH2Cl2/MeOH) to afford the desired product (110.6 mg, 0.468 mmol, 51% yield). MS (ESI pos. ion) m/z (MH+): 237. Calc'd exact mass for C11H12N2O2S: 236. 1H NMR (400 MHz, CDCl3): 8.21 (s, 1H), 7.53 (s, 1H), 7.12 (s, 1H), 6.88 (s, 1H), 4.14 (t, J=5.0 Hz, 2H), 4.02 (q, J=5.0 Hz, 2H), 2.33 (s, 1H, J=5.0 Hz, 1H), 2.28 (s, 3H).

後処理

  1. customplaced in a preheated oil bath
  2. temperaturewas then cooled to room temperature
  3. customquenched with saturated sodium bicarbonate (5 mL)
  4. waitto stand at room temperature overnight
  5. extractionIt was then extracted with CH2Cl2 and with 10:1 CH2Cl2/MeOH
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. filtrationfiltered through silica gel (30:1 CH2Cl2/MeOH)

出典と根拠

ORDレコード
ord-0a7e9277f68f4b249bc76b98a229dcba
出典データセット
uspto-grants-2012_11
特許番号
US08314087B2

反応ノート

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