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

HRID 1829048

반응식

HRID 1829048 반응식
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

참가 물질

8

반응물 3

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

생성물 1

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

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 887Methanol용매HCID 6228Dimethylformamide용매

반응 조건

온도
65 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-be0939c8a573433199b87c0311c98046
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07060844B2

연결된 노트

불러오는 중…