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1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 8-(2-Chloro-4-fluorophenyl)-N-(1-(6-methylpyrimidin-4-yl)piperidin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

HRID 451455
ノート
印刷プレビュー

反応式

HRID 451455 の反応式
Cl.Cl.[CH3:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]([N:10]2[CH2:15][CH2:14][CH:13]([NH2:16])[CH2:12][CH2:11]2)[CH:5]=1.Br[C:18]1[N:34]=[C:21]2[C:22]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=3[Cl:33])=[CH:23][CH:24]=[CH:25][N:20]2[N:19]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.[O-]C1C=CC=CC=1.[Na+]>ClCCl.O1CCOCC1>[Cl:33][C:27]1[CH:28]=[C:29]([F:32])[CH:30]=[CH:31][C:26]=1[C:22]1[C:21]2[N:20]([N:19]=[C:18]([NH:16][CH:13]3[CH2:14][CH2:15][N:10]([C:6]4[CH:5]=[C:4]([CH3:3])[N:9]=[CH:8][N:7]=4)[CH2:11][CH2:12]3)[N:34]=2)[CH:25]=[CH:24][CH:23]=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 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 4445035Phenolate SodiumHCID 673364492-Bromo-8-(2-chloro-4-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridineHCID 673421331-(6-Methylpyrimidin-4-yl)piperidin-4-amine dihydrochloride

生成物 1

HCID 533537188-(2-Chloro-4-fluorophenyl)-N-(1-(6-methylpyrimidin-4-yl)piperidin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine
収率 44.3%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
130 °C

実験手順

1-(6-Methylpyrimidin-4-yl)piperidin-4-amine dihydrochloride (133 mg, 0.5 mmol) was suspended in dichloromethane (15 mL) and then extracted with aqueous sodium hydroxide (2 M, 10 mL). The aqueous layer was extracted with dichloromethane (15 mL) and the organic layers were combined, dried over sodium sulfate and evaporated carefully. After addition of 2-bromo-8-(2-chloro-4-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyridine (180 mg, 0.55 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (23.1 mg, 0.04 mmol), tris(dibenzylideneacetone)dipalladium(o) chloroform adduct (21 mg, 0.02 mmol) and sodium phenoxide (87 mg, 0.75 mmol) in dry 1,4-dioxane (4 mL) the reaction mixture was stirred under an argon atmosphere for 60 minutes at 130° C. in the microwave. Concentration and purification of the residue by chromatography (SiO2, heptane:ethyl acetate 3:1 to 0:1) afforded the title compound as yellow foam (97 mg, 44%).

後処理

  1. extractionextracted with aqueous sodium hydroxide (2 M, 10 mL)
  2. extractionThe aqueous layer was extracted with dichloromethane (15 mL)
  3. dry with materialdried over sodium sulfate
  4. customevaporated carefully
  5. concentrationConcentration and purification of the residue by chromatography (SiO2, heptane:ethyl acetate 3:1 to 0:1)

出典と根拠

ORDレコード
ord-dad9f949b52d456f8bc8466615647673
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08486967B2

反応ノート

読み込み中…

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