Water → 2-(5-[1,3]Dioxolan-2-yl-2,4-dimethoxy-phenyl)-pyrazine

HRID 10664

反応式

HRID 10664 の反応式
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[C:7]([O:23][CH3:24])=[CH:8][C:9]([O:21][CH3:22])=[C:10](B2OC(C)(C)C(C)(C)O2)[CH:11]=1.I[C:26]1[CH:31]=[N:30][CH:29]=[CH:28][N:27]=1.C([O-])([O-])=O.[Na+].[Na+].O>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[C:7]([O:23][CH3:24])=[CH:8][C:9]([O:21][CH3:22])=[C:10]([C:26]2[CH:31]=[N:30][CH:29]=[CH:28][N:27]=2)[CH:11]=1

参加物

7

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 642841IodopyrazineHCID 161156182-(5-(1,3-Dioxolan-2-yl)-2,4-dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

生成物 1

HCID 219809982-(5-[1,3]Dioxolan-2-yl-2,4-dimethoxy-phenyl)-pyrazine収率 59%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

Ex-46C: 2-(5-[1.3]Dioxolan-2-yl-2,4-dimethoxy-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (Ex-46B, 2.22 g, 6.60 mmol, containing borolane impurity) was dissolved in DME (60 mL) and 2-iodopyrazine (0.59 mL, 6.0 mmol) was added. 2M aqueous Na2CO3 (17.8 mL, 35.6 mmol) was added and the mixture was purged with nitrogen for 20 min. Tetrakis(triphenylphosphine)palladium(0) (0.69 g, 0.60 mmol) was added and the mixture was heated at reflux for 2.5 h. After cooling, water (50 mL) was added and the mixture was extracted with CH2Cl2 (2×30 mL). The organic phase was washed with brine (1×20 mL), dried over sodium sulfate, filtered, and concentrated. Purification of the resulting yellow-orange solids via silica chromatography (50–80% EtOAc/hexanes) provided 1.02 g of 2-(5-[1,3]dioxolan-2-yl-2,4-dimethoxy-phenyl)-pyrazine as a yellow solid (59% yield). 1H-NMR (CDCl3) δ 9.10 (d, J=2 Hz, 1H), 8.61 (m, 1H), 8.39 (d, J=3 Hz, 1H), 8.07 (s, 1H), 6.57 (s, 1H), 6.14 (s, 1H), 4.13–4.18 (m, 2H), 4.01–4.05 (m, 2H), 3.95 (s, 3H), 3.93 (s, 3H).

後処理

  1. customthe mixture was purged with nitrogen for 20 min
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 2.5 h
  4. temperatureAfter cooling
  5. extractionthe mixture was extracted with CH2Cl2 (2×30 mL)
  6. washThe organic phase was washed with brine (1×20 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification of the resulting yellow-orange solids via silica chromatography (50–80% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-1c1ac17fdab24ec4b251ad30815eb2e7
出典データセット
uspto-grants-2006_08
特許番号
US07094801B2

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