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Ethanethiol → 5-Ethylsulfanyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester

HRID 1930814
ノート
印刷プレビュー

反応式

HRID 1930814 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[Na+].[CH2:24]([SH:26])[CH3:25]>O1CCOCC1.C(OCC)(=O)C.O1CCCC1.C(P(C(C)C)[C-]1C=CC=C1)(C)C.[C-]1(P(C(C)C)C(C)C)C=CC=C1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([S:26][CH2:24][CH3:25])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
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

8

反応物 3

HCID 6343EthanethiolHCID 16102683N-Boc-5-bromoisoindolineHCID 23676156Sodium t-butoxide

生成物 1

HCID 577536005-Ethylsulfanyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒
HCID 15420033
Bis(cyclopenta-2,4-dien-1-yl-di(propan-2-yl)phosphane);iron(2+)
触媒
HCID 312751,4-Dioxane溶媒
HCID 21939870Tetrahydrofuran ethyl acetate溶媒

反応条件

温度
100 °C

実験手順

Lit. Tetrahedron 2004, 60, 7397-7403. To a stirred suspension of 1.34 mmol 5-bromo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (CAS: 201940-08-1) in 2 ml dioxane were added 0.03 mmol 1,1′-bis(diisopropylphosphino)ferrocene, 0.03 mmol palladium acetate, 1.61 mmol sodium tert-butoxide and 2.68 mmol ethanethiol and the mixture was stirred at 100° C. for 16 h. The reaction mixture was then cooled to room temperature, diluted with ethyl acetate/tetrahydrofuran and washed with brine. The organic phase was dried over sodium sulfate and concentrated in vacuo to yield the title compound as a brown oil which was used in the next step without further purification.

後処理

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. washwashed with brine
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-8ce8b68a559d4ea68f089b0496c5fbda
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08188139B2

反応ノート

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