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Sodium Carbonate → 3-(2-tert-butylphenyl)-1-(phenylsulfonyl)-1H-indole

HRID 2423217
ノート
印刷プレビュー

反応式

HRID 2423217 の反応式
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](B(O)O)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)S(O[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]([CH3:37])([CH3:36])[CH3:35])(=O)=O.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:34]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:10]([S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[CH:11]=1)([CH3:37])([CH3:36])[CH3:35]
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 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 27762171-(phenylsulfonyl)-1H-indol-3-ylboronic acidHCID 187792072-(Tert-butyl)phenyl trifluoromethanesulfonate

生成物 1

HCID 672419373-(2-tert-butylphenyl)-1-(phenylsulfonyl)-1H-indole収率 92%

試薬・触媒・溶媒 3

HCID 178418397
HCID 178418397、化合物
触媒
HCID 962Water溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
150 °C

実験手順

1-(Phenylsulfonyl)-1H-indol-3-ylboronic acid (150.9 mg, 0.501 mmol), 2-tert-butylphenyl trifluoromethanesulfonate (255 mg, 0.902 mmol) and tetrakis(triphenylphosphine)palladium (0) (58 mg, 0.050 mmol) are combined in a septa capped microwave vial and placed under an argon atmosphere. Degassed solutions of 2 M sodium carbonate (0.75 mL, 1.50 mmol) and of dioxane (2.5 mL) were introduced and the vial heated to 150° C. for 15 minutes in a microwave reactor. The cooled reaction mixture was diluted with water and ethyl acetate, the phases separated and the aqueous extracted twice more with ethyl acetate. The combined extracts were washed with water, brine, dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography eluting with a gradient of ethyl acetate and hexanes to give 3-(2-tert-butylphenyl)-1-(phenylsulfonyl)-1H-indole (175.8 mg, 92%) as a colorless gummy solid.

後処理

  1. customcapped microwave vial
  2. customThe cooled reaction mixture
  3. customthe phases separated
  4. extractionthe aqueous extracted twice more with ethyl acetate
  5. washThe combined extracts were washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with a gradient of ethyl acetate and hexanes

出典と根拠

ORDレコード
ord-2feede511ec445e48403e3681e1b83cf
出典データセット
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07960569B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート