Potassium Carbonate → 3'-({[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}methyl)-2-fluoro-3-biphenylcarboxamide

HRID 657351ノート

反応式

HRID 657351 の反応式
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+].Br[C:27]1[C:28]([F:36])=[C:29]([CH:33]=[CH:34][CH:35]=1)[C:30]([NH2:32])=[O:31].[CH3:37][C:38]([Si:41]([CH3:54])([CH3:53])[O:42][CH2:43][C:44]1[CH:45]=[C:46](B(O)O)[CH:47]=[CH:48][CH:49]=1)([CH3:40])[CH3:39]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:40][C:38]([Si:41]([CH3:54])([CH3:53])[O:42][CH2:43][C:44]1[CH:45]=[C:46]([C:27]2[CH:35]=[CH:34][CH:33]=[C:29]([C:30]([NH2:32])=[O:31])[C:28]=2[F:36])[CH:47]=[CH:48][CH:49]=1)([CH3:37])[CH3:39]

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 442031023-Bromo-2-fluorobenzamideHCID 57813382[3-({[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]boronic acid

生成物 1

HCID 578133053'-({[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}methyl)-2-fluoro-3-biphenylcarboxamide収率 63%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

Pd(OAc)2 (123.6 mg, 0.55 mmol), PPh3 (557.5 mg, 2.2 mmol), K2CO3 (3.8 g, 27.5 mmol) and 3-bromo-2-fluorobenzamide (4.0 g, 18.4 mmol) were suspended in 1,4-dioxane (30 mL). After the mixture was heated to 80° C. for 15 min, [3-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]boronic acid (5.9 g, 22.0 mmol) was added. Then the reaction mixture was stirred over night at 100° C. After cooling to room temperature, the solvent was removed under reduced pressure. The residue was dissolved in CH2Cl2 (50 mL), then was washed with water (20 mL), brine (20 mL), and dried over Na2SO4. After the solvent was removed, the crude product was purified on an Al2O3 column chomatography, eluting with CH2Cl2/CH3OH (300:1). 3′-({[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}methyl)-2-fluoro-3-biphenylcarboxamide, was obtained (4.1 g, yield: 63%). 1H NMR (400 MHz, CDCl3) δ 0.12 (s, 6H), 0.95 (s, 9H), 4.81 (s, 2H), 7.25-8.12 (m, 7H).

後処理

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in CH2Cl2 (50 mL)
  4. washwas washed with water (20 mL), brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. customAfter the solvent was removed
  7. customthe crude product was purified on an Al2O3 column chomatography
  8. washeluting with CH2Cl2/CH3OH (300:1)

出典と根拠

ORDレコード
ord-8f6b07a1492642e1a178505b44044591
出典データセット
uspto-grants-2011_12
特許番号
US08071588B2

反応ノート

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