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Cesium carbonate → 4-[2-(3-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-6-pyridin-3-yl-pyrimidine

HRID 965690
ノート
印刷プレビュー

反応式

HRID 965690 の反応式
Cl[C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[C:13]2[C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][N:18]=2)[N:5]=[CH:4][N:3]=1.[N:24]1[CH:29]=[CH:28][CH:27]=[C:26](B(O)O)[CH:25]=1.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.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]>[F:23][C:22]1[C:17]([C:13]2[N:12]([CH2:11][C:6]3[C:7]([CH2:8][CH2:9][CH3:10])=[C:2]([C:26]4[CH:25]=[N:24][CH:29]=[CH:28][CH:27]=4)[N:3]=[CH:4][N:5]=3)[CH:16]=[CH:15][N:14]=2)=[N:18][CH:19]=[CH:20][CH:21]=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

7

反応物 4

HCID 10796Cesium carbonateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 27343783-Pyridinylboronic acidHCID 100423524-Chloro-6-{[2-(3-fluoro-2-pyridinyl)-1H-imidazol-1-yl]methyl}-5-propylpyrimidine

生成物 1

HCID 100680004-[2-(3-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-6-pyridin-3-yl-pyrimidine

試薬・触媒・溶媒 2

HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A mixture of 4-chloro-6-[2-(3-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidine (268 mg, 0.81 mmol), 3-pyridyl boronic acid (1.84 mmol), Pd2(dba)3 (37 mg, 0.04 mmol), (t-Bu)3P (8 mg, 0.04 mmol) and Cs2CO3 (600 mg, 1.84 mmol) in dioxane (6 mL) is degassed. The mixture is then heated at 100° C. for 6 hours. The solvent is removed in vacuo and water (10 mL) and EtOAc (15 mL) is added. The layers are separated and the aqueous layer is extracted with EtOAc (15 mL). The combined extracts are washed with brine (20 mL), dried (Na2SO4), and evaporated. Preparative TLC purification of the residue provides the title product. 1H NMR (CDCl3) 8.95 (s, 1H), 8.69 (s, 2H), 8.24 (d, 1H), 7.79 (d, 1H), 7.51 (t, 1H), 7.40-7.43 (m, 1H), 7.32 (s, 1H), 7.21-7.25 (m, 1H), 7.19 (s, 1H), 5.91 (s, 2H), 2.65-2.69 (m, 2H), 1.41-1.47 (m, 2H), 0.81 (t, 3H).

後処理

  1. customis degassed
  2. customThe solvent is removed in vacuo and water (10 mL) and EtOAc (15 mL)
  3. additionis added
  4. customThe layers are separated
  5. extractionthe aqueous layer is extracted with EtOAc (15 mL)
  6. washThe combined extracts are washed with brine (20 mL)
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customPreparative TLC purification of the residue

出典と根拠

ORDレコード
ord-a9be3b2fbd4445f8b0a87495b8a7e909
出典データセット
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06951864B2

反応ノート

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