Benzyl mercaptan → 7-(Benzylthio)-4-chloroquinoline

HRID 1473410

반응식

HRID 1473410 반응식
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([Cl:12])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.O1CCOCC1.CCN(C(C)C)C(C)C.[CH2:28]([SH:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O.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].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>[CH2:28]([S:35][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([Cl:12])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

참가 물질

8

반응물 4

HCID 7509Benzyl mercaptanHCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 108002397-Bromo-4-Chloroquinoline

생성물 1

HCID 866874577-(Benzylthio)-4-chloroquinoline수율 89%

시약·촉매·용매 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매

실험 절차

A 250-mL 3-neck round-bottom flask was charged with 7-bromo-4-chloroquinoline (BioBlocks, Inc., San Diego, Calif.; 7.000 g, 28.9 mmol), Xantphos (0.835 g, 1.443 mmol), and Pd2(dba)3 (0.661 g, 0.722 mmol), and after flushing with argon, dioxane (57.7 ml) and n,n-diisopropylethylamine (10.08 ml, 57.7 mmol) were added in sequence. The flask was fitted with a reflux condenser, and was placed in a heating bath at 80° C. for 10 minutes, after which benzyl mercaptan (3.58 ml, 30.3 mmol) was added drop wise via syringe. The reaction was stirred for 20 minutes until completion. The material was diluted with water, and washed with DCM (×3), and the combined organics were dried via phase separator (Radley's Technology) and concentrated under a vacuum. Upon dissolving the material in DCM, solids remained out of solution, and they were filtered off and washed with DCM. The corresponding filtrate was concentrated under a vacuum and purified via silica gel chromatography (120-g column) eluting with 0 to 100% ethyl acetate in heptanes to yield 7-(benzylthio)-4-chloroquinoline (7.35 g, 25.7 mmol, 89% yield) as a light yellow solid. m/z (ESI) 286.0 (M+H)+.

후처리

  1. additionwere added in sequence
  2. customThe flask was fitted with a reflux condenser
  3. washwashed with DCM (×3)
  4. customthe combined organics were dried via phase separator (Radley's Technology)
  5. concentrationconcentrated under a vacuum
  6. dissolutionUpon dissolving the material in DCM
  7. filtrationwere filtered off
  8. washwashed with DCM
  9. concentrationThe corresponding filtrate was concentrated under a vacuum
  10. custompurified via silica gel chromatography (120-g column)
  11. washeluting with 0 to 100% ethyl acetate in heptanes

출처 및 근거

ORD 기록
ord-ea8141a6744f44db846ca66751ba2da8
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012443B2

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