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Sodium Carbonate → HCID 131727401、化合物

HRID 2110282
ノート
印刷プレビュー

反応式

HRID 2110282 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+]>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: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 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 92.9%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒
HCID 962
Water
溶媒
HCID 8857Ethyl Acetate溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

A solution of 7 g of 4-cyano-2,3-difluorophenyl trifluoromethanesulfonate in 400 mL of dioxane is admixed at ambient temperature with 8.67 g of N-Boc 4-amino-3-fluorophenylboronic acid, 7.235 g of sodium carbonate in solution in 100 mL of distilled water, and then 3.38 g of tetrakistriphenylphosphinepalladium. The reaction mixture is heated at 90° C. for 3 h and then concentrated to dryness under reduced pressure. The solid obtained is taken up in ethyl acetate; this organic phase is washed a number of times with distilled water and then with saturated 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 7.89 g of tert-butyl(4′-cyano-3,2′,3′-trifluorobiphenyl-4-yl)carbamate in the form of a cream-white solid, whose characteristics are as follows:

後処理

  1. concentrationconcentrated to dryness under reduced pressure
  2. customThe solid obtained
  3. washthis organic phase is washed a number of times with distilled water
  4. dry with materialwith saturated sodium chloride solution, dried over magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe solid obtained
  7. customis chromatographed on a silica column (eluent: cyclohexane/ethyl acetate, 90/10 by volume)
  8. customEvaporation to dryness under reduced pressure of the fractions
  9. additioncontaining the expected product

出典と根拠

ORDレコード
ord-2b066b5b6ca74d3e8aa2298fbbd3e305
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

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