Nitrogen → HCID 89708471、化合物

HRID 1845896ノート

反応式

HRID 1845896 の反応式
Br[C:2]1[CH:3]=[C:4]([O:9][C@H:10]([C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[C:14]([F:19])[C:13]=2[Cl:20])[CH3:11])[C:5]([NH2:8])=[N:6][CH:7]=1.C(N(CC)CC)C.N#N.[C:30]([Si:32]([CH3:35])([CH3:34])[CH3:33])#[CH:31]>C1(C)C=CC=CC=1.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:20][C:13]1[C:14]([F:19])=[CH:15][CH:16]=[C:17]([Cl:18])[C:12]=1[C@@H:10]([O:9][C:4]1[C:5]([NH2:8])=[N:6][CH:7]=[C:2]([C:31]#[C:30][Si:32]([CH3:35])([CH3:34])[CH3:33])[CH:3]=1)[CH3:11]

参加物

8

反応物 4

HCID 947NitrogenHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 848193465-Bromo-3-[(1S)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-2-pyridinamine

生成物 1

HCID 89708471HCID 89708471、化合物収率 80.6%

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
30 °C

実験手順

The compound (S)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-aminopyridine (12.58 g, 33.11 mmol) was dispersed in toluene (100 mL), and triethylamine (14.05 g, 139.06 mmol) and copper iodide (126 mg, 0.66 mmol) were added successively. Under the protection of N2 atmosphere, PdCl2(PPh3)2 (465 mg, 0.66 mmol) was added. The reaction mixture was heated to 30° C., stirred for 0.5 h. Ethynyltrimethylsilane (9.11 g, 92.71 mmol) was added dropwise, gradually warmed to 90° C., and stirred overnight. Through HPLC test, it was found that the raw materials were completely reacted. The reaction liquid was cooled down, washed with water, and the toluene layers were combined. The toluene layer was dried over anhydrous Na2SO4, concentrated; the residue was purified via silica gel column chromatography (petroleum ether:ethyl acetate=3:1) to yield the target product as yellow solid (10.6 g, yield: 80%).

後処理

  1. temperaturegradually warmed to 90° C.
  2. stirringstirred overnight
  3. customwere completely reacted
  4. customThe reaction liquid
  5. temperaturewas cooled down
  6. washwashed with water
  7. dry with materialThe toluene layer was dried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. customthe residue was purified via silica gel column chromatography (petroleum ether:ethyl acetate=3:1)

出典と根拠

ORDレコード
ord-885d4328091247e39848fa7a4aae587a
出典データセット
uspto-grants-2015_02
特許番号
US08952002B2

反応ノート

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