Potassium Carbonate → (E)-ethyl 3-(3-(tert-butoxycarbonylamino)-4-chlorophenyl)acrylate

HRID 631169

反応式

HRID 631169 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:16])=[C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].CC1(C)C(C)(C)OB(/[CH:31]=[CH:32]/[C:33]([O:35][CH2:36][CH3:37])=[O:34])O1>C(#N)C.CCO.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:11]([O:10][C:9]([NH:8][C:6]1[CH:7]=[C:2](/[CH:31]=[CH:32]/[C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:3]=[CH:4][C:5]=1[Cl:16])=[O:15])([CH3:14])([CH3:13])[CH3:12]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 23553751(E)-Ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylateHCID 57840526tert-butyl N-(5-bromo-2-chlorophenyl)carbamate

生成物 1

HCID 67067541(E)-ethyl 3-(3-(tert-butoxycarbonylamino)-4-chlorophenyl)acrylate

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
100 °C

実験手順

To a solution of tert-butyl 5-bromo-2-chlorophenylcarbamate (1) (1.0 equiv.) in acetonitrile (0.3M) and EtOH (0.5M) was added K2CO3 (2.0 equiv.). The reaction was degassed and flushed with N2, then added (E)-ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate (2) (1.2 equiv.) and Pd(PPh3)4 (0.1 equiv.). The reaction was flushed again with N2 and stirred at 100° C. overnight. After cooling to room temperature, hexane was added, and the mixture was filtered through a pad of silica, eluting with EA/Hex (1:1) until the product was completely eluted. The filtrate was concentrated and purified on Combiflash, eluting with 0-15% EA in Hex to give (E)-ethyl 3-(3-(tert-butoxycarbonylamino)-4-chlorophenyl)acrylate (3) as a white solid.

後処理

  1. customThe reaction was degassed
  2. customflushed with N2
  3. customThe reaction was flushed again with N2
  4. temperatureAfter cooling to room temperature
  5. additionhexane was added
  6. filtrationthe mixture was filtered through a pad of silica
  7. washeluting with EA/Hex (1:1) until the product
  8. washwas completely eluted
  9. concentrationThe filtrate was concentrated
  10. custompurified on Combiflash
  11. washeluting with 0-15% EA in Hex

出典と根拠

ORDレコード
ord-0ce24bd14d2d4f8bbfdf1f8e2b30fd60
出典データセット
uspto-grants-2016_04
特許番号
US09320748B2

関連ノート

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