(NZ)-N-(7-bromo-3-chloro-1-fluorochromeno[2,3-c]pyridin-5-ylidene)-2-methylpropane-2-sulfinamide → tert-butyl 2-(7-bromo-3-chloro-5-(1,1-dimethylethylsulfinamido)-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)acetate

HRID 931569ノート

反応式

HRID 931569 の反応式
[Cl-].[C:2]([O:6][C:7](=[O:10])[CH2:8][Zn+])([CH3:5])([CH3:4])[CH3:3].[Br:11][C:12]1[CH:13]=[C:14]2[C:25](=[CH:26][CH:27]=1)[O:24][C:17]1[C:18]([F:23])=[N:19][C:20]([Cl:22])=[CH:21][C:16]=1/[C:15]/2=[N:28]\[S:29]([C:31]([CH3:34])([CH3:33])[CH3:32])=[O:30]>C1COCC1.CCOC(C)=O>[Br:11][C:12]1[CH:13]=[C:14]2[C:25](=[CH:26][CH:27]=1)[O:24][C:17]1[C:18]([F:23])=[N:19][C:20]([Cl:22])=[CH:21][C:16]=1[C:15]2([CH2:8][C:7]([O:6][C:2]([CH3:5])([CH3:4])[CH3:3])=[O:10])[NH:28][S:29]([C:31]([CH3:34])([CH3:33])[CH3:32])=[O:30]

参加物

5

反応物 2

HCID 87400620(NZ)-N-(7-bromo-3-chloro-1-fluorochromeno[2,3-c]pyridin-5-ylidene)-2-methylpropane-2-sulfinamideHCID 178451183HCID 178451183、化合物

生成物 1

HCID 86658360tert-butyl 2-(7-bromo-3-chloro-5-(1,1-dimethylethylsulfinamido)-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)acetate収率 59.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

A solution of (2-tert-butoxy-2-oxoethyl)zinc(II) chloride (0.5M in Et2O; 116 mL, 57.9 mmol) was cooled to 0° C. and a solution of (Z)—N-(7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-ylidene)-2-methylpropane-2-sulfinamide (10 g, 23.16 mmol) in THF (100 mL) was added drop wise. The resulting mixture was stirred at for 1 hour 0° C. The reaction mixture was diluted with EtOAc and washed with aqueous saturated solution of NH4Cl, followed by brine. The organic layer was dried over Na2SO4, and concentrated under reduced pressure. The obtained residue was purified by chromatography (0-20% EtOAc/hexanes) to afford tert-butyl 2-(7-bromo-3-chloro-5-(1,1-dimethylethylsulfinamido)-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)acetate (7.5 g, 13.69 mmol, 59.1% yield) as a yellow solid.

後処理

  1. washwashed with aqueous saturated solution of NH4Cl
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by chromatography (0-20% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-b7473fd86e414b3c849f637ee3e5f50f
出典データセット
uspto-grants-2016_03
特許番号
US09296759B2

反応ノート

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