Sodium Carbonate → 3-Phenylimidazo[1,2-a]pyrazine

HRID 1893402ノート

反応式

HRID 1893402 の反応式
Br[C:2]1[N:6]2[CH:7]=[CH:8][N:9]=[CH:10][C:5]2=[N:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[C:17]1([C:2]2[N:6]3[CH:7]=[CH:8][N:9]=[CH:10][C:5]3=[N:4][CH:3]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 27716713-Bromoimidazo(1,2-a)pyrazine2 回

生成物 1

HCID 208103403-Phenylimidazo[1,2-a]pyrazine収率 88%

試薬・触媒・溶媒 3

HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

3-Bromoimidazo[1,2-a]pyrazine (1.66 g, 7.13 mmol, Intermediate 2), sodium carbonate (3.78 g, 35.6 mmol) and phenylboronic acid (1.043 g, 8.55 mmol) were dissolved in 1,2-dimethoxyethane (DME) (40 ml) and water (20 ml). Bis(triphenylphosphine)palladium (II) chloride (0.250 g, 0.356 mmol) was added and the biphasic solution heated at 80° C. for 16 h. The aqueous phase was extracted with ethyl acetate (3×100 ml) and the combined extracts washed with saturated sodium bicarbonate solution (100 ml), water (100 ml), brine (100 ml) and dried by passing through a hydromatrix cartridge (Varian). The filtrate was concentrated in vacuo to afford a crude oil (2.44 g). The crude product was purified by flash chromatography (Biotage SP4, 40+M, eluting with a 0-100% gradient of ethylacetate in hexane)—(the product elutes in 100% ethyl acetate), to afford 3-phenylimidazo[1,2-a]pyrazine (1.22 g, 6.25 mmol, 88% yield).

後処理

  1. extractionThe aqueous phase was extracted with ethyl acetate (3×100 ml)
  2. washthe combined extracts washed with saturated sodium bicarbonate solution (100 ml), water (100 ml), brine (100 ml)
  3. customdried
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto afford a crude oil (2.44 g)
  6. customThe crude product was purified by flash chromatography (Biotage SP4, 40+M
  7. washeluting with a 0-100% gradient of ethylacetate in hexane)—(the product

出典と根拠

ORDレコード
ord-7bbf034828d5441aa441ce65425fc294
出典データセット
uspto-grants-2013_08
特許番号
US08513248B2

反応ノート

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