Triethylamine → 3-[5-(3-dimethylamino-prop-1-ynyl)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-one

HRID 1829048

反応式

HRID 1829048 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[C:11]1[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]1=[O:20])[O:6][CH2:5]2.[CH3:21][N:22]([CH3:26])[CH2:23][C:24]#[CH:25].C(N(CC)CC)C>CN(C=O)C.CO.[Cu]I.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>[CH3:21][N:22]([CH3:26])[CH2:23][C:24]#[C:25][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[C:11]1[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]1=[O:20])[O:6][CH2:5]2

参加物

8

反応物 3

HCID 8471TriethylamineHCID 81643N,N-DimethylpropargylamineHCID 696592423-(5-Bromo-2-benzofuran-1(3H)-ylidene)-1,3-dihydro-2H-indol-2-one

生成物 1

HCID 696591513-[5-(3-dimethylamino-prop-1-ynyl)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-one収率 68.2%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
65 °C

実験手順

To a mixture of 3-(5-bromo-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one (467 mg, 1.42 mmol), 1-dimethylamino-2-propyne (473 mg, 5.69 mmol), copper(I) iodide (48 mg, 0.25 mmol), triethylamine (287 mg, 2.84 mmol) in DMF (5 ml), was added tetrakis(triphenylphosphine)palladium (100 mg, 0.086 mmol). The mixture was heated at 65° C. under argon for 16 hours, and then cooled to room temperature. The mixture was diluted with MeOH (100 ml). The insoluble material was removed by filtration, and the filtrate solution was concentrated and then diluted with EtOAc (200 ml). The resulting mixture was washed with brine (3×100 ml), dried over anhydrous Na2SO4, and concentrated to give a dark-brown residue. Purification of the residue by silica gel column chromatography, eluted with a gradient of MeOH in CHCl3, afforded 3-[5-(3-dimethylamino-prop-1-ynyl)-3H-isobenzofuran-1-ylidene]-1,3-dihydro-indol-2-one as a brown solid (320 mg, 68%).

後処理

  1. temperaturecooled to room temperature
  2. customThe insoluble material was removed by filtration
  3. concentrationthe filtrate solution was concentrated
  4. additiondiluted with EtOAc (200 ml)
  5. washThe resulting mixture was washed with brine (3×100 ml)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customto give a dark-brown residue
  9. customPurification of the residue by silica gel column chromatography
  10. washeluted with a gradient of MeOH in CHCl3

出典と根拠

ORDレコード
ord-be0939c8a573433199b87c0311c98046
出典データセット
uspto-grants-2006_06
特許番号
US07060844B2

関連ノート

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