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Triethylamine → 3,6-Dichloro-2-[(6-chloropyridin-3-ylthio)(pyridin-4-yl)methyl]pyridine

HRID 2080431
ノート
印刷プレビュー

反応式

HRID 2080431 の反応式
[Cl:1][C:2]1[C:3]([CH:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)O)=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[Cl:29][C:30]1[N:35]=[CH:34][C:33]([SH:36])=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>CCCCCC.C(OCC)(=O)C.CN(C)C=O.ClCCl>[Cl:1][C:2]1[C:3]([CH:9]([S:36][C:33]2[CH:34]=[N:35][C:30]([Cl:29])=[CH:31][CH:32]=2)[C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

10

反応物 5

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 14158786-Chloropyridine-3-thiolHCID 23028600(3,6-Dichloropyridin-2-yl) (pyridine-4-yl)methanol

生成物 1

HCID 231147773,6-Dichloro-2-[(6-chloropyridin-3-ylthio)(pyridin-4-yl)methyl]pyridine収率 36%

試薬・触媒・溶媒 4

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a dichloromethane (3 ml) solution of the (3,6-dichloropyridin-2-yl)(pyridin-4-yl)methanol (153 mg, 0.60 mmol) obtained in Referential Example 25 were added triethylamine (0.167 ml, 1.20 mmol) and methanesulfonyl chloride (0.070 ml, 0.90 mmol) sequentially at 0° C. The resulting mixture was stirred at room temperature for 2 hours. After the reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate, the organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. To an N,N-dimethylformamide (3 ml) solution of the residue thus obtained were added an N,N-dimethylformamide (2 ml) solution of 6-chloro-3-pyridinethiol and then, potassium carbonate (100 mg, 0.72 mmol). The resulting mixture was stirred at room temperature for 18 hours. To the reaction mixture was added ethyl acetate. The resulting mixture was washed with a saturated aqueous solution of sodium bicarbonate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel chromatography. The fraction obtained from the hexane:ethyl acetate=7:3 eluate was concentrated under reduced pressure to give the title compound (83 mg, 0.22 mmol, 36%) as a yellow oil.

後処理

  1. washAfter the reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customTo an N,N-dimethylformamide (3 ml) solution of the residue thus obtained
  6. stirringThe resulting mixture was stirred at room temperature for 18 hours
  7. washThe resulting mixture was washed with a saturated aqueous solution of sodium bicarbonate
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customThe residue thus obtained
  12. concentrationethyl acetate=7:3 eluate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-b7e2d75d18b740dfab71ad19312a5e74
出典データセット
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07932271B2

反応ノート

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