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Dimethylformamide → (3-Chloro-5-cyano-2-fluoro-benzyl)-carbamic acid tert-butyl ester

HRID 1527473
ノート
印刷プレビュー

反応式

HRID 1527473 の反応式
[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][C:9]1[CH:14]=[C:13](Br)[CH:12]=[C:11]([Cl:16])[C:10]=1[F:17])([CH3:4])([CH3:3])[CH3:2].[CH3:19][N:20](C=O)C>[C-]#N.[Zn+2].[C-]#N.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:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([C:19]#[N:20])[CH:12]=[C:11]([Cl:16])[C:10]=1[F:17])([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

5

反応物 2

HCID 6228DimethylformamideHCID 68283623Carbamic acid, N-[(5-bromo-3-chloro-2-fluorophenyl)methyl]-, 1,1-dimethylethyl ester

生成物 1

HCID 68283962(3-Chloro-5-cyano-2-fluoro-benzyl)-carbamic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒

反応条件

温度
120 °C

実験手順

To a solution of (5-bromo-3-chloro-2-fluoro-benzyl)-carbamic acid tert-butyl ester (3 g, 8.86 mmol) in DMF (45 mL) was added zinc cyanide (1.04 g, 8.86 mmol) and Pd(Ph3P)4 (1.02 g, 0.886 mmol). The reaction mixture was stirred at 120° C. for 15 min in a microwave apparatus (Personal Chemistry, Biotage). After cooling to RT, the mixture was filtered through Celite and rinsed down with EtOAc. The filtrate was washed with saturated aqueous NH4Cl solution (4×75 mL), dried (Na2SO4) and evaporated in vacuo. Purification by flash column chromatography on silica gel (eluent gradient: c-hexane/EtOAc 9:1 to 3:1) afforded the title compound as white solid. TLC Rf (c-hexane/EtOAc 3:1)=0.35; tR (HPLC conditions c): 5.28 min.

後処理

  1. temperatureAfter cooling to RT
  2. filtrationthe mixture was filtered through Celite
  3. washrinsed down with EtOAc
  4. washThe filtrate was washed with saturated aqueous NH4Cl solution (4×75 mL)
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo
  7. customPurification by flash column chromatography on silica gel (eluent gradient: c-hexane/EtOAc 9:1 to 3:1)

出典と根拠

ORDレコード
ord-abc2ebf9d0604c8ba7cf414ddde6e604
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09085555B2

反応ノート

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