Ethyl Acetate → HCID 50993867、化合物

HRID 1784831ノート

反応式

HRID 1784831 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[CH:12][N:13]3[Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])O1.[Br:29][C:30]1[CH:35]=[C:34]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=2)[CH:33]=[C:32](I)[CH:31]=1.C(=O)([O-])[O-].[Na+].[Na+].CCOC(C)=O>C(O)C.C1(C)C=CC=CC=1.O.[Cl-].[Na+].O>[Br:29][C:30]1[CH:31]=[C:32]([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[CH:12][N:13]3[Si:18]([CH:25]([CH3:26])[CH3:27])([CH:22]([CH3:23])[CH3:24])[CH:19]([CH3:21])[CH3:20])[CH:33]=[C:34]([O:36][CH2:37][C:38]2[CH:39]=[CH:40][C:41]([O:44][CH3:45])=[CH:42][CH:43]=2)[CH:35]=1

参加物

9

反応物 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 27955744-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)-1-(triisopropylsilyl)-1H-indoleHCID 509940261-Bromo-3-iodo-5-(4-methoxy-benzyloxy)-benzene

生成物 1

HCID 50993867HCID 50993867、化合物収率 91.3%

試薬・触媒・溶媒 4

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
90 °C

実験手順

A 1 L flask was charged with 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-triisopropylsilanyl-1H-indole (17.44 g, 43.67 mmol) and 1-Bromo-3-iodo-5-(4-methoxy-benzyloxy)-benzene (18.30 g, 43.67 mmol) in ethanol (180 mL) and toluene (180 mL) under argon. Tetrakis-triphenylphosphin-palladium (1.51 g, 1.31 mmol) was added. Then a solution of sodium carbonate (9.26 g, 87.34 mmol) in water (92.6 mL) was added and the mixture heated to 90° C. and stirred for 14 h. After cooling down to room temperature AcOEt (300 mL) and brine (200 mL) were added under stirring. The mixture was filtered through a pad of Hyflo. After separation of the layers the aqueous one was extracted with AcOEt (2×300 mL). The combined organic layers were washed with water and brine (150 mL), dried over Na2SO4, filtered and evaporated to dryness. After flash chromatography on silica gel (1 kg, AcOEt/heptane 1:19) 4-[3-bromo-5-(4-methoxy-benzyloxy)-phenyl]-1-triisopropylsilanyl-1H-indole (22.5 g, 91%) was obtained as a colorless oil.

後処理

  1. additionwere added
  2. stirringunder stirring
  3. filtrationThe mixture was filtered through a pad of Hyflo
  4. customAfter separation of the layers the aqueous one
  5. extractionwas extracted with AcOEt (2×300 mL)
  6. washThe combined organic layers were washed with water and brine (150 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated to dryness

出典と根拠

ORDレコード
ord-248392b0c6ba4032a2242aa879019276
出典データセット
uspto-grants-2009_03
特許番号
US07504401B2

反応ノート

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