Diisopropylethylamine → 5-Iodo-2-tritylisoindoline

HRID 710282

반응식

HRID 710282 반응식
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([I:9])=[CH:5][C:4]=1[CH2:10]Br.[C:12]([NH2:31])([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[I:9][C:6]1[CH:5]=[C:4]2[C:3](=[CH:8][CH:7]=1)[CH2:2][N:31]([C:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH2:10]2

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 138598TritylamineHCID 667267221,2-Bis(bromomethyl)-4-iodobenzene

생성물 1

HCID 667262485-Iodo-2-tritylisoindoline수율 48%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

A mixture of the product of Step B (0.34 g; 0.87 mmol) hydrochloride salt of tritylamine (0.22 g; 0.87 mmol) and N,N-diisopropylethylamine (DIPEA) (0.49 ml; 2.8 mmol) in anhydrous DMF (3 ml) was stirred for 2 h at 60° C. under N2. After removing the solvent in vacuo, the residue was diluted to 15 ml with ethyl acetate (EtOAc) and washed with, H2O, brine and dried over anhydrous MgSO4 and filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was purified by FCC (SiO2; hexane/EtOAc, 8:2) to give pure title compound (0.2 g; 48%) as colourless heavy syrup. 1H-NMR (CDCl3) 3.86 (s, 2H); 3.87 (s, 2H); 6.81-7.57 (m, 18H).

후처리

  1. customAfter removing the solvent in vacuo
  2. additionthe residue was diluted to 15 ml with ethyl acetate (EtOAc)
  3. washwashed with, H2O, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness under reduced pressure
  7. customthe residue was purified by FCC (SiO2; hexane/EtOAc, 8:2)

출처 및 근거

ORD 기록
ord-2b25a432ae864e688dac041a97b72a02
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181182B2

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