Benzyl mercaptan → HCID 86687567、化合物

HRID 1473513ノート

反応式

HRID 1473513 の反応式
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([Cl:12])=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[F:13].O1CCOCC1.CCN(C(C)C)C(C)C.[CH2:29]([SH:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=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>[CH2:29]([S:36][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([Cl:12])=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[F:13])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

参加物

8

反応物 4

HCID 7509Benzyl mercaptanHCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 866875667-Bromo-4-chloro-6-fluoroquinoline

生成物 1

HCID 86687567HCID 86687567、化合物収率 90%

試薬・触媒・溶媒 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒

実験手順

A vial was charged with 7-bromo-4-chloro-6-fluoroquinoline (0.141 g, 0.541 mmol), Xantphos (0.016 g, 0.027 mmol), and Pd2(dba)3 (0.012 g, 0.014 mmol) and after flushing with argon, dioxane (1.083 ml) and n,n-diisopropylethylamine (0.189 ml, 1.083 mmol) were added in sequence. The vial was sealed, and was placed in a heating bath at 80° C. for 10 minutes, after which benzylmercaptan (0.067 ml, 0.568 mmol) was added drop wise via syringe. The reaction was stirred for 30 minutes. The material was diluted with water, and washed with DCM (×3), and the combined organics were dried via phase separator and concentrated in vacuo. The material was purified via silica gel chromatography eluting with 0-50% ethyl acetate in heptane to yield 7-(benzylthio)-4-chloro-6-fluoroquinoline (0.148 g, 0.487 mmol, 90% yield) as a light yellow solid. m/z (ESI) 304.2 (M+H)+.

後処理

  1. additionwere added in sequence
  2. customThe vial was sealed
  3. washwashed with DCM (×3)
  4. customthe combined organics were dried via phase separator
  5. concentrationconcentrated in vacuo
  6. customThe material was purified via silica gel chromatography
  7. washeluting with 0-50% ethyl acetate in heptane

出典と根拠

ORDレコード
ord-366928f18483436fba902f7fe720b7b0
出典データセット
uspto-grants-2015_04
特許番号
US09012443B2

反応ノート

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