Iodine → HCID 91379151、化合物

HRID 857369ノート

反応式

HRID 857369 の反応式
II.Br[CH:4]=[CH:5][CH3:6].[CH3:7][O:8][C:9](=[O:26])[CH2:10][CH:11]1[C:15]2=[CH:16][C:17]3[C:18](Br)=[CH:19][C:20]([O:23][CH3:24])=[CH:21][C:22]=3[N:14]2[CH2:13][CH2:12]1>C1COCC1.[Zn+2].[Br-].[Br-].[Pd].[Cu]I>[CH3:7][O:8][C:9](=[O:26])[CH2:10][CH:11]1[C:15]2=[CH:16][C:17]3[C:18]([C:5]([CH3:6])=[CH2:4])=[CH:19][C:20]([O:23][CH3:24])=[CH:21][C:22]=3[N:14]2[CH2:13][CH2:12]1

参加物

8

反応物 3

HCID 807IodineHCID 115331-Bromo-1-propeneHCID 58760742HCID 58760742、化合物

生成物 1

HCID 91379151HCID 91379151、化合物

試薬・触媒・溶媒 4

HCID 23938Palladium触媒HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 10421208Zinc bromide触媒HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
60 °C

実験手順

To Mg (143 mg, 5.8 mmol) in THF (4 mL) with trace of I2 was added α-bromopropene (583 μL) in order to maintain a 60° C. exotherm. After 30 minutes, a solution of ZnBr2 (1.31 g, 5.8 mmol) in THF (4 mL) was added. The reaction mixture was heated at 55° C. for 1 hour, cooled to r.t. and (Pd (dppf) CH2Cl2 (50 mg) was added followed by CuI (18.5 mg). After 5 minutes a solution of methyl (8-bromo-6-methoxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (Example 22, Step 5, 200 mg, 0.59 mmol) in THF (7 mL) was added and the mixture was refluxed for 1 hour, cooled, quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography to give the title compound (50 mg).

後処理

  1. temperatureThe reaction mixture was heated at 55° C. for 1 hour
  2. temperaturecooled to r.t.
  3. temperaturethe mixture was refluxed for 1 hour
  4. temperaturecooled
  5. customquenched with saturated aqueous NH4Cl
  6. extractionextracted with EtOAc
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-0854fb48adbd470db0cf99307948342c
出典データセット
uspto-grants-2006_12
特許番号
US07144913B2

反応ノート

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