Triethylamine → HCID 58046440、化合物

HRID 2046407ノート

反応式

HRID 2046407 の反応式
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7](Br)=[C:8]([C:10]2[N:14]3[N:15]=[CH:16][CH:17]=[CH:18][C:13]3=[N:12][CH:11]=2)[CH:9]=1)=[O:4].[CH:20]([B-](F)(F)F)=[CH2:21].[K+].C(N(CC)CC)C>C(O)CC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH:20]([C:7]1[S:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:9][C:8]=1[C:10]1[N:14]2[N:15]=[CH:16][CH:17]=[CH:18][C:13]2=[N:12][CH:11]=1)=[CH2:21]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 58046405Methyl 5-bromo-4-(imidazo[1,2-b]pyridazin-3-yl)thiophene-2-carboxylate

生成物 1

HCID 58046440HCID 58046440、化合物

試薬・触媒・溶媒 2

HCID 178418807HCID 178418807、化合物触媒HCID 10311-Propanol溶媒

反応条件

温度
100 °C

実験手順

Methyl-5-bromo-4-(imidazo[1,2-b]pyridazin-3-yl)thiophene-2-carboxylate (200 mg, 0.591 mmol), potassium vinyltrifluoroborate (119 mg, 0.887 mmol), PdCl2(dppf)-CH2Cl2 adduct (48 mg, 0.059 mmol), and triethylamine (0.165 mL, 1.18 mmol) was dissolved in n-propanol (5.91 mL) and purged with nitrogen for 5 minutes in a sealed tube. The solution was heated at 100° C. for 18 h. the reaction was cooled to room temperature and quenched with saturated sodium bicarbonate. The aqueous layer was extracted with ethyl acetate (×3) and the organic layers combined, dried with magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography to afford the title compound as an orange solid. 1H NMR (500 MHz, CD3SOCD3) δ 8.61 (d, 1H); 8.23 (d, 1H); 8.16 (s, 1H); 7.95 (s, 1H); 7.32 (dd, 1H); 6.94 (dd, 1H); 5.87 (d, 1H); 5.44 (d, 1H); 3.85 (s, 3H). LRMS (APCI) calc'd for (C14H11N3O2S) [M+11]+, 286.1. found 286.0.

後処理

  1. custompurged with nitrogen for 5 minutes in a sealed tube
  2. temperaturewas cooled to room temperature
  3. customquenched with saturated sodium bicarbonate
  4. extractionThe aqueous layer was extracted with ethyl acetate (×3)
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-0380dd10f42642c48eda19af5f695715
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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