Morpholine → 4-(6-Bromopyridin-3-yl)morpholine

HRID 661465노트

반응식

HRID 661465 반응식
C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+].[NH:49]1[CH2:54][CH2:53][O:52][CH2:51][CH2:50]1.[Br:55][C:56]1[CH:61]=[CH:60][C:59](I)=[CH:58][N:57]=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C.O>[Br:55][C:56]1[N:57]=[CH:58][C:59]([N:49]2[CH2:54][CH2:53][O:52][CH2:51][CH2:50]2)=[CH:60][CH:61]=1

참가 물질

9

반응물 4

HCID 8083MorpholineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 47382712-Bromo-5-iodopyridineHCID 23676156Sodium t-butoxide

생성물 1

HCID 230921314-(6-Bromopyridin-3-yl)morpholine

시약·촉매·용매 4

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

Tris(dibenzylideneacetone)dipalladium (840 mg) and 4,5-bis(diphenyl-phosphino)-9,9-dimethylxanthene (1.6 g) and sodium tert-butoxide (6.6 g) were added to a solution of morpholine (2 ml) and 2-bromo-5-iodo-pyridine (7.8 g) in toluene (230 ml), and the mixture was stirred under nitrogen atmosphere at room temperature overnight. Water and ethyl acetate were added to the mixture and the organic layer was separated, washed with a saturated brine, dried over magnesium sulfate and concentrated in vacuo. The resulting residue was purified by column chromatography (silica gel; hexane:ethyl acetate=9:1→7:3) to give the titled compound (5.07 g). MS (m/z): 243/245 [M+H]+.

후처리

  1. customthe organic layer was separated
  2. washwashed with a saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by column chromatography (silica gel; hexane:ethyl acetate=9:1→7:3)

출처 및 근거

ORD 기록
ord-53b301b4ef07439286be831dcb394ad9
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084611B2

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