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2-(Tributylstannyl)-1,3-thiazole → 3-[2-(6-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-4-propyl-6-thiazol-2-yl-pyridazine

HRID 1244264
ノート
印刷プレビュー

反応式

HRID 1244264 の反応式
Cl[C:2]1[N:7]=[N:6][C:5]([CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[N:15]=2)=[C:4]([CH2:21][CH2:22][CH3:23])[CH:3]=1.C([Sn](CCCC)(CCCC)[C:29]1[S:30][CH:31]=[CH:32][N:33]=1)CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:20][C:16]1[N:15]=[C:14]([C:10]2[N:9]([CH2:8][C:5]3[N:6]=[N:7][C:2]([C:29]4[S:30][CH:31]=[CH:32][N:33]=4)=[CH:3][C:4]=3[CH2:21][CH2:22][CH3:23])[CH:13]=[CH:12][N:11]=2)[CH:19]=[CH:18][CH:17]=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

5

反応物 2

HCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 103820556-Chloro-3-[2-(6-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-4-propyl-pyridazine

生成物 1

HCID 104298633-[2-(6-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-4-propyl-6-thiazol-2-yl-pyridazine

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140
Toluene
溶媒

反応条件

温度
100 °C

実験手順

A mixture of 6-chloro-3-[2-(6-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-4-propyl-pyridazine (268 mg, 0.81 mmol), 2-tributylstannanyl-thiazole (453 mg, 1.21 mmol), and Pd(PPh3)4 (0.08 mmol, 93 mg) in toluene (10 mL) is degassed. The mixture is then heated at 100° C. overnight. Saturated KF aqueous solution (8 mL) is added and the mixture is stirred for 15 minutes. The layers are separated and the aqueous layer is extracted with EtOAc (10 mL). The combined extracts are washed with brine (15 mL), dried (Na2SO4), and evaporated. Preparative TLC (5% methanol in DCM) purification of the residue provides the title product. 1H NMR (CDCl3) 8.14–8.18 (m, 2H), 7.97 (d, 1H0, 7.83 (q, 1H), 7.50 (d, 1H), 7.20 (d, 1H), 7.18 (d, 1H), 6.80 (dd, 1H), 6.28 (s, 2H), 2.80 (t, 2H), 1.62–1.73 (m, 2H), 0.97 (t, 3H).

後処理

  1. customis degassed
  2. additionSaturated KF aqueous solution (8 mL) is added
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with EtOAc (10 mL)
  5. washThe combined extracts are washed with brine (15 mL)
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customPreparative TLC (5% methanol in DCM) purification of the residue

出典と根拠

ORDレコード
ord-7519edfd623d4a2a94ddf779f93d0515
出典データセット
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07122546B2

反応ノート

読み込み中…

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