Benzyl mercaptan → 3-(Benzylthio)-8-chloro-1,7-naphthyridine

HRID 1473492노트

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HRID 1473492 반응식
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[N:7][C:6]=2[Cl:12].CCN(C(C)C)C(C)C.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[CH2:64]([SH:71])[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=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].O1CCOCC1>[CH2:64]([S:71][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[N:7][C:6]=2[Cl:12])[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1

참가 물질

7

반응물 4

HCID 7509Benzyl mercaptanHCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 722135923-Bromo-8-chloro-1,7-naphthyridine

생성물 1

HCID 866875473-(Benzylthio)-8-chloro-1,7-naphthyridine수율 51.4%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

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온도
40 °C

실험 절차

To a vial charged with 3-bromo-8-chloro-1,7-naphthyridine (Anichem, North Brunswick, N.J.) (360 mg, 1.479 mmol) was added dioxane (5914 μl), DIEA (516 μl, 2.96 mmol), Xantphos (171 mg, 0.296 mmol), Pd2(dba)3 (135 mg, 0.148 mmol) and benzyl mercaptan (184 μl, 1.552 mmol). The vessel was sealed and heated to 40° C. overnight. The mixture was cooled to RT, filtered through diatomaceous earth and dried under reduced pressure. The crude residue was purified with a 25 g silicycle HP column (25 μm spherical silica) ramping EtOAc in heptane (0 to 100%, 10% DCM throughout) to provide 3-(benzylthio)-8-chloro-1,7-naphthyridine (0.218 g, 0.760 mmol, 51.4% yield) as a light yellow solid. m/z (ESI) 287.1 (M+H)+.

후처리

  1. customThe vessel was sealed
  2. temperatureThe mixture was cooled to RT
  3. filtrationfiltered through diatomaceous earth
  4. customdried under reduced pressure
  5. customThe crude residue was purified with a 25 g silicycle HP column (25 μm spherical silica)

출처 및 근거

ORD 기록
ord-7fda61ab3e1c4552887a8dbc746bba69
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012443B2

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