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Hydrochloric Acid → Ethyl 3-[1-(p-bromobenzyl)-5-methoxy-2-methylindol-3-yl]-4,4,4-trifluorobutanoat

HRID 1451527
ノート
印刷プレビュー

反応式

HRID 1451527 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2[CH:13]([C:20]([F:23])([F:22])[F:21])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[Br:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39]Br)=[CH:37][CH:36]=1.Cl>C1COCC1>[Br:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39][N:8]2[C:9]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)[C:6]([CH:13]([C:20]([F:23])([F:22])[F:21])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:7]2[CH3:12])=[CH:37][CH:36]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 685274-Bromobenzyl bromideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 19974941Ethyl 3-(5-methoxy-2-methylindol-3-yl)-4,4,4-trifluorobutanoate

生成物 1

HCID 19974932Ethyl 3-[1-(p-bromobenzyl)-5-methoxy-2-methylindol-3-yl]-4,4,4-trifluorobutanoat収率 64%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a -78° C. solution of the indole from Step 3 (3.1 g, 9.4 mmol) in 65 mL of THF was added KHMDS (0.6M toluene solution, 18.8 mL, 11.3 mmol) dropwise. The solution was warmed to 0° C., then cooled to -78° C. A solution of p-bromobenzyl bromide (3.0 g, 12.2 mmol) was then added, and the solution was allowed to warm to room temperature. The solution was then poured into 1M HCl and extracted with ether. The organic extracts were washed with brine, dried over MgSO4 and evaporated. The residue was purified by flash chromatography (20% ethyl acetate/hexanes) to provide 3.0 g of the title compound.

後処理

  1. temperaturecooled to -78° C
  2. temperatureto warm to room temperature
  3. extractionextracted with ether
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe residue was purified by flash chromatography (20% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-ea5fb29cbd5944c0a7f547a1785b3b58
出典データセット
uspto-grants-1997_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05604253

反応ノート

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