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Sodium Carbonate → tert-Butyl 4-((2-chloro-5-phenylpyridin-4-ylamino)methyl)piperidine-1-carboxylate

HRID 384697
ノート
印刷プレビュー

反応式

HRID 384697 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[C:5](I)=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:30]1(B(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(#N)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[C:5]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:4][N:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 59613389Tert-butyl 4-(((2-chloro-5-iodopyridin-4-yl)amino)methyl)piperidine-1-carboxylate

生成物 1

HCID 59613323tert-Butyl 4-((2-chloro-5-phenylpyridin-4-ylamino)methyl)piperidine-1-carboxylate収率 99.5%

試薬・触媒・溶媒 2

HCID 11979704
Tetrakis(triphenylphosphine)palladium
触媒
HCID 6342Acetonitrile溶媒

実験手順

A solution of tert-butyl 4-((2-chloro-5-iodopyridin-4-ylamino)methyl)piperidine-1-carboxylate (0.100 g, 0.22 mmol), sodium carbonate (0.5 M, 0.66 mL), phenyl boronic acid (0.027 g, 0.221 mmol) and tetrakis(triphenylphosphine) palladium(0) (0.011 g, 0.01 mmol) in acetonitrile (2 mL) was heated at 100° C. for 20 min under microwave irradiation. The reaction mixture was concentrated in vacuo. The crude product was purified by chromatography on a short silica column, eluting with ethyl acetate/petroleum ether (3/7), to give the title compound as a colourless oil (0.088 g, 98%).

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe crude product was purified by chromatography on a short silica column
  3. washeluting with ethyl acetate/petroleum ether (3/7)

出典と根拠

ORDレコード
ord-5cb3fc62552040bc8d4676e7a1f49b98
出典データセット
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08367658B2

反応ノート

読み込み中…

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