Sodium Carbonate → HCID 178419025、化合物

HRID 10417

反応式

HRID 10417 の反応式
Br[C:2]1[CH:18]=[CH:17][C:5]2[NH:6][C:7]([CH2:9][CH2:10][N:11]3[CH2:15][CH2:14][CH2:13][CH:12]3[CH3:16])=[N:8][C:4]=2[CH:3]=1.[C:19]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)#[N:20].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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].C(Cl)Cl>[CH3:16][C@@H:12]1[CH2:13][CH2:14][CH2:15][N:11]1[CH2:10][CH2:9][C:7]1[NH:6][C:5]2[CH:17]=[CH:18][C:2]([C:24]3[CH:25]=[CH:26][C:21]([C:19]#[N:20])=[CH:22][CH:23]=3)=[CH:3][C:4]=2[N:8]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 178418858HCID 178418858、化合物

生成物 1

HCID 178419025HCID 178419025、化合物収率 40.4%

試薬・触媒・溶媒 3

HCID 178418807HCID 178418807、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

Nitrogen (N2) gas was bubbled through a solution of 5-bromo-2-[2-(2-methyl-pyrrolidin-1-yl)-ethyl]-1H-benzoimidazole (0.19 g, 0.6 mmol) and 4-cyanophenylboronic acid (0.13 g, 0.9 mmol) in 1,2-dimethoxyethane (4 mL) and H2O (2 mL). To the mixture was added 2M Na2CO3 (1.2 mL, 2.4 mmol) and Pd(dppf)2Cl2:CH2Cl2 (1:1), and this mixture heated to 80° C. After approximately 24 h, the reaction mixture was cooled and extracted with ethyl acetate. The organic layer was then washed with H2O and distilled to dryness. The crude product was purified by column chromatography to afford the title compound (0.08 g). 1H NMR (400 MHz, CDCl3) δ 1.18 (d, 3H), 1.52–1.62 (m, 1H), 1.77–1.95 (m, 2H), 2.03–2.12 (m, 1H), 2.30 (q, 1H), 2.47–2.56 (m, 1H), 2.57–2.62 (m, 1H), 3.15–3.20 (m, 2H), 3.21–3.35 (m, 2H), 7.43 (dd, J=1.7 & 8.3, 1H), 7.62 (d, 1H), 7.68–7.73 (m, 4H), 7.76 (s, 1H); 13C NMR (400 MHz, CDCl3) δ 19.5, 22.2, 27.4, 33.2, 51.5, 53.3, 60.5, 109.9, 118.9, 121.2, 127.5, 132.2, 133.0, 146.1, 156.1 (2 peaks overlapping and some 13C peaks were not readily identified due to exchange broadening). APP-IMS: (M+1)+ at 331 m/z.

後処理

  1. temperaturethe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was then washed with H2O
  4. distillationdistilled to dryness
  5. customThe crude product was purified by column chromatography

出典と根拠

ORDレコード
ord-14f696dcbf5a4434a0b46e260bb5ebf6
出典データセット
uspto-grants-2006_08
特許番号
US07094790B2

関連ノート

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