Cesium carbonate → Methyl 4-bromo-3-formyl-1-[3-(1-naphthalenyloxy)propyl]-1H-indole-2-carboxylate

HRID 533260노트

반응식

HRID 533260 반응식
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH:15]=[O:16])=[C:5]([C:11]([O:13][CH3:14])=[O:12])[NH:6]2.Br[CH2:18][CH2:19][CH2:20][O:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C.O>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH:15]=[O:16])=[C:5]([C:11]([O:13][CH3:14])=[O:12])[N:6]2[CH2:18][CH2:19][CH2:20][O:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 129593811-(3-Bromopropoxy)naphthaleneHCID 71463951Methyl 4-bromo-3-formyl-1H-indole-2-carboxylate

생성물 1

HCID 87353272Methyl 4-bromo-3-formyl-1-[3-(1-naphthalenyloxy)propyl]-1H-indole-2-carboxylate

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of EXAMPLE 107A (1.76 g) in N,N-dimethylformamide (10 mL) was added 1-(3-bromopropoxy)naphthalene (1.66 g) and Cs2CO3 (6.10 g). The mixture was stirred for 3 days at room temperature. The mixture was diluted with ethyl acetate (300 mL) and water (200 mL). The aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with water (×3) and brine and dried over Na2SO4. After filtration, concentration of solvent gave crude product, which was purified by column chromatography (5% ethyl acetate in hexane).

후처리

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. washThe combined organic extracts were washed with water (×3) and brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration, concentration of solvent
  5. customgave crude product, which
  6. customwas purified by column chromatography (5% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-6ea4b6766b1a41c3808bfedde8ae15e8
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853209B2

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