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Toluene → 4-(benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine

HRID 910889
ノート
印刷プレビュー

反応式

HRID 910889 の反応式
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH3:7])[N:6]=1.[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18](Cl)[CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].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].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]([NH:1][C:2]2[S:3][CH:4]=[C:5]([CH3:7])[N:6]=2)[CH:17]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 534041974-(Benzyloxy)-2-chloropyridine

生成物 1

HCID 866347144-(benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine収率 48%

試薬・触媒・溶媒 3

HCID 636044
1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)
触媒
HCID 9811564Bis(dibenzylideneacetone)palladium触媒
HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

A 250 mL round-bottomed flask was charged with 2-amino-4-methylthiazole (43.8 mL, 17.5 mmol), 4-(benzyloxy)-2-chloropyridine (4.23 g, 19.3 mmol), potassium phosphate (4.09 g, 19.3 mmol), and toluene (44 mL), and the reaction mixture was degassed with nitrogen. Tris(dibenzylideneacetone)-dipalladium (0) (0.401 g, 0.438 mmol) and 9,9-dimethyl-4,5-bis(diphenyl-phosphino)-xanthene (0.279 g, 0.482 mmol) were added, and the reaction mixture was degassed with nitrogen. The reaction mixture was warmed to 90° C., degassed water (15 mL) was added, and reaction mixture was stirred at 90° C. overnight. Water was added, and the reaction mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and filtered through a small plug of silica gel, and the filtrate was concentrated down to 50 mL of ethyl acetate and filtered to afford 4-(benzyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine (2.50 g, 47.5% yield) as a white solid. 1H NMR (CDCl3) δ 9.29 (bs, 1H), 8.15 (d, 1H), 7.39 (m, 4H), 7.35 (m, 1H), 6.53 (dd, 1H), 6.41 (d, 1H), 6.36 (d, 1H), 5.07 (s, 2H), 2.33 (s, 3H). Mass spectrum (esi) m/z=298 (M

後処理

  1. customthe reaction mixture was degassed with nitrogen
  2. customthe reaction mixture was degassed with nitrogen
  3. customdegassed water (15 mL)
  4. additionwas added
  5. customreaction mixture
  6. extractionthe reaction mixture was extracted with ethyl acetate
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered through a small plug of silica gel
  9. concentrationthe filtrate was concentrated down to 50 mL of ethyl acetate
  10. filtrationfiltered

出典と根拠

ORDレコード
ord-9e1bc0a8e00348de9b492dea08001071
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08022222B2

反応ノート

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