Potassium Phosphate, Tribasic → Methyl 4-(imidazo[1,2-b]pyridazin-3-yl)-5-methylthiophene-2-carboxylate

HRID 2046402ノート

反応式

HRID 2046402 の反応式
Br[C:2]1[N:6]2[N:7]=[CH:8][CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[CH3:11][O:12][C:13]([C:15]1[S:16][C:17]([CH3:29])=[CH:18][C:19]=1B1OC(C)(C)C(C)(C)O1)=[O:14].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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].O1CCOCC1>[N:4]1[CH:3]=[C:2]([C:18]2[CH:19]=[C:15]([C:13]([O:12][CH3:11])=[O:14])[S:16][C:17]=2[CH3:29])[N:6]2[C:5]=1[CH:10]=[CH:9][CH:8]=[N:7]2

参加物

7

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 128723193-Bromoimidazo(1,2-b)pyridazineHCID 46702783Methyl 5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate

生成物 1

HCID 58046374Methyl 4-(imidazo[1,2-b]pyridazin-3-yl)-5-methylthiophene-2-carboxylate

試薬・触媒・溶媒 2

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

反応条件

温度
100 °C

実験手順

3-Bromoimidazo[1,2-b]pyridazine (0.40 g, 2.02 mmol), methyl-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate (0.86 g, 3.03 mmol), Pd2(dba)3 (0.19 g, 0.20 mmol), tricyclohexylphosphine (0.14 g, 0.51 mmol), aqueous tribasic potassium phosphate (1.27 M, 1.45 mL, 6.85 mmol), and 1,4-dioxane (10.1 mL) were placed in a flask and purged with nitrogen for five minutes. The solution was heated to 100° C. for four hours. The solution was cooled to room temperature, poured into an aqueous solution of saturated sodium bicarbonate, and extracted with ethyl acetate (×3). The combined organic layers were dried with magnesium sulfate, filtered, and concentrated and the residue purified by flash chromatography to afford the title compound as a yellow solid. 1H NMR (500 MHz, CD3SOCD3) δ 8.62 (d, 1H); 8.24 (s, 1H); 8.21 (d, 1H); 8.06 (s, 1H); 7.30 (dd, 1H); 3.83 (s, 3H); 2.58 (s, 3H). LRMS (APCI) calc'd for (C13H11N3O2S) [M+H]+, 274.0. found 274.0.

後処理

  1. custompurged with nitrogen for five minutes
  2. temperatureThe solution was cooled to room temperature
  3. additionpoured into an aqueous solution of saturated sodium bicarbonate
  4. extractionextracted with ethyl acetate (×3)
  5. dry with materialThe combined organic layers were dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe residue purified by flash chromatography

出典と根拠

ORDレコード
ord-c14b9daa6c6641fd9eed24d5ea36888a
出典データセット
uspto-grants-2013_11
特許番号
US08592425B2

反応ノート

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