Sodium Carbonate → 3-[6-[2-[(2-Methylpropan-2-yl)oxycarbonylamino]propanoylamino]-2-(2-phenylethynyl)pyridin-3-yl]benzoic acid

HRID 535416ノート

反応式

HRID 535416 の反応式
[C:1]([O:5][C:6](=[O:28])[NH:7][CH:8]([CH3:27])[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15](Br)=[C:14]([C:19]#[C:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:13]=1)=[O:10])([CH3:4])([CH3:3])[CH3:2].B([C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][CH:40]=1)[C:35]([OH:37])=[O:36])(O)O.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>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.O.CO>[CH3:2][C:1]([O:5][C:6]([NH:7][CH:8]([CH3:27])[C:9]([NH:11][C:12]1[N:13]=[C:14]([C:19]#[C:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]([C:32]2[CH:33]=[C:34]([CH:38]=[CH:39][CH:40]=2)[C:35]([OH:37])=[O:36])=[CH:16][CH:17]=1)=[O:10])=[O:28])([CH3:4])[CH3:3]

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 27339573-Carboxyphenylboronic acidHCID 86694405tert-butyl-N-[1-[[5-bromo-6-(2-phenylethynyl)pyridin-2-yl]amino]-1-oxo-propan-2-yl]carbamate

生成物 1

HCID 866944043-[6-[2-[(2-Methylpropan-2-yl)oxycarbonylamino]propanoylamino]-2-(2-phenylethynyl)pyridin-3-yl]benzoic acid

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

A mixture of tert-butyl-N-[1-[[5-bromo-6-(2-phenylethynyl)pyridin-2-yl]amino]-1-oxopropan-2-yl]carbamate C2d (40 mg, 0.09 mmol), 3-boronobenzoic acid (18 mg, 0.11 mmol), Dichlorobis(triphenylphosphine)palladium(II) (6.3 mg, 0.01 mmol), Na2CO3 (19 mg, 0.18 mmol), dioxane (0.9 ml), MeOH (0.2 ml) and water (0.1 ml) is stirred under argon atmosphere for 4 h at 70° C. The reaction mixture is concentrated in vacuo and the product purified by RP HPLC. Yield: 16 mg (37%). HPLC-MS: M+H=486; tR=1.49 min (*Method—5).

後処理

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customthe product purified by RP HPLC

出典と根拠

ORDレコード
ord-49ba016946ab4b9380984cd12eef0da3
出典データセット
uspto-grants-2014_10
特許番号
US08859541B2

反応ノート

読み込み中…