Morpholine → 2-(1-ethyl-6-fluoro-4-hydroxy-1H-indol-3-yl)-1-morpholinoethanone

HRID 1404099노트

반응식

HRID 1404099 반응식
[CH2:1]([N:3]1[C:11]2[C:6](=[C:7]([OH:13])[CH:8]=[C:9]([F:12])[CH:10]=2)[C:5]([CH2:14][C:15]([OH:17])=O)=[CH:4]1)[CH3:2].[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.O>[CH2:1]([N:3]1[C:11]2[C:6](=[C:7]([OH:13])[CH:8]=[C:9]([F:12])[CH:10]=2)[C:5]([CH2:14][C:15]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[O:17])=[CH:4]1)[CH3:2]

참가 물질

7

반응물 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 583039722-(1-ethyl-6-fluoro-4-hydroxy-1H-indol-3-yl)acetic acid

생성물 1

HCID 583040262-(1-ethyl-6-fluoro-4-hydroxy-1H-indol-3-yl)-1-morpholinoethanone수율 91.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of compounds 11-3 (119 mg, 0.5 mmol) in DMF (2 mL) was added morpholine (66 uL, 0.75 mmol), triethylamine (0.24 mL, 1.75 mmol) and BOP (265 mg, 0.6 mmol). The reaction mixture was stirred at room temperature overnight. The solution was diluted with water and extracted with EtOAc. Combined organic layers were washed with 1N HCl, water, brine, dried over MgSO4, filtered and concentrated. The crude material was purified by flash chromatography (silica gel, ethyl acetate:hexanes: 25:75 to 100%) gave pure 11-4 (140 mg, 91%) as a white foam.

후처리

  1. extractionextracted with EtOAc
  2. washCombined organic layers were washed with 1N HCl, water, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by flash chromatography (silica gel, ethyl acetate:hexanes: 25:75 to 100%)

출처 및 근거

ORD 기록
ord-54c252789ac54488855cdf85c131c9fd
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912220B2

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