Dichloromethane → 2,2-dimethyl-1-[2-(3,4,5-trimethoxy-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-pent-4-en-1-one

HRID 1677514ノート

反応式

HRID 1677514 の反応式
Br[C:2]1[N:3]=[C:4]2[C:10]([C:11](=[O:18])[C:12]([CH3:17])([CH3:16])[CH2:13][CH:14]=[CH2:15])=[CH:9][N:8]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[C:5]2=[N:6][CH:7]=1.[CH3:27][O:28][C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[C:33]([O:37][CH3:38])[C:34]=1[O:35][CH3:36].C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>O1CCOCC1.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]>[CH3:16][C:12]([CH3:17])([CH2:13][CH:14]=[CH2:15])[C:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([C:31]3[CH:32]=[C:33]([O:37][CH3:38])[C:34]([O:35][CH3:36])=[C:29]([O:28][CH3:27])[CH:30]=3)[N:3]=2)[N:8]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH:9]=1)=[O:18]

参加物

8

反応物 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 27343903,4,5-Trimethoxybenzeneboronic acidHCID 595406911-[2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-pent-4-en-1-one

生成物 1

HCID 595408992,2-dimethyl-1-[2-(3,4,5-trimethoxy-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-pent-4-en-1-one収率 72.1%

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of impure 1-[2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-pent-4-en-1-one (0.900 g, “2.05 mmol), 3,4,5-trimethoxyphenyl boronic acid (0.479 g, 2.26 mmol), potassium carbonate (0.850 g, 6.15 mmol) and Pd(dppf)Cl2.CH2Cl2 (0.171 g, 0.21 mmol) in 15 mL of 1,4-dioxane and 4 mL of water was stirred at 120° C. in a microwave for 1 h. The resulting mixture was partitioned between 300 mL of ethyl acetate and 200 mL of water. The organic layer was dried over MgSO4, filtered and concentrated to a residue. Column chromatography (0→35% EtOAc/hexanes) afforded 0.777 g (29% for three steps from 2-bromo-5H-pyrrolo[2,3-b]pyrazine) of 2,2-dimethyl-1-[2-(3,4,5-trimethoxy-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-pent-4-en-1-one.

後処理

  1. customThe resulting mixture was partitioned between 300 mL of ethyl acetate and 200 mL of water
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to a residue

出典と根拠

ORDレコード
ord-5ed26acf7e4040aeb892c1fd3ff964bf
出典データセット
uspto-grants-2011_08
特許番号
US08008298B2

反応ノート

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