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

HRID 535416노트

반응식

HRID 535416 반응식
[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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
70 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-49ba016946ab4b9380984cd12eef0da3
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859541B2

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