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Water → HCID 131727401、化合物

HRID 2110280
ノート
印刷プレビュー

反応式

HRID 2110280 の反応式
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[C:9]([F:15])[C:8]=1[F:16])(=O)=O.[C:19]([NH:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][C:28]=1[F:36])([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C(=O)([O-])[O-].[Na+].[Na+].O>O1CCOCC1.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:22]([O:21][C:19](=[O:20])[NH:26][C:27]1[CH:32]=[CH:31][C:30]([C:7]2[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[C:9]([F:15])[C:8]=2[F:16])=[CH:29][C:28]=1[F:36])([CH3:25])([CH3:23])[CH3:24]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962Water2 回HCID 10340Sodium CarbonateHCID 222886774-N-Boc-Amino-3-fluorophenylboronic acidHCID 57636526HCID 57636526、化合物

生成物 1

HCID 131727401HCID 131727401、化合物収率 16.5%

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 312751,4-Dioxane溶媒

実験手順

A solution of 3.75 g of 4-cyano-2,3-difluorophenyl trifluoromethanesulfonate in 220 mL of dioxane is admixed at ambient temperature with 5 g of N-Boc-4-amino-3-fluorophenylboronic acid, 3.87 g of sodium carbonate in solution with 56 mL of distilled water and then 1.81 g of tetrakistriphenylphosphinepalladium. The reaction mixture is heated for 3 h at reflux and then poured, after cooling, into the distilled water. This mixture is extracted with ethyl acetate, the organic phase is decanted, washed a number of times with distilled water, then with saturated aqueous sodium chloride solution, dried over magnesium sulfate and then concentrated to dryness under reduced pressure. The solid obtained is chromatographed on a silica column (eluent: cyclohexane/ethyl acetate, 90/10 by volume). Evaporation to dryness under reduced pressure of the fractions containing the expected product gives 0.75 g of tert-butyl(4′-cyano-3,2′,3′-trifluorobiphenyl-4-yl)carbamate in the form of a pale pink solid, whose characteristics are as follows:

後処理

  1. temperatureThe reaction mixture is heated for 3 h
  2. temperatureat reflux
  3. additionpoured
  4. extractionThis mixture is extracted with ethyl acetate
  5. customthe organic phase is decanted
  6. washwashed a number of times with distilled water
  7. dry with materialwith saturated aqueous sodium chloride solution, dried over magnesium sulfate
  8. concentrationconcentrated to dryness under reduced pressure
  9. customThe solid obtained
  10. customis chromatographed on a silica column (eluent: cyclohexane/ethyl acetate, 90/10 by volume)
  11. customEvaporation to dryness under reduced pressure of the fractions
  12. additioncontaining the expected product

出典と根拠

ORDレコード
ord-a6f6af1fccd64d249d434cda7bad0c78
出典データセット
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07517902B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート