Sodium Carbonate → 1,1-Dimethylethyl N-((4-hydroxy-1,1-dimethyl-2-oxo-6-(3-pyridinyl)-naphthalen-3-yl)carbonyl)glycinate

HRID 2078048ノート

反応式

HRID 2078048 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[C:7](=[O:14])[C:6]([C:15]([NH:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:16])=[C:5]2[OH:26].[N:27]1[CH:32]=[CH:31][CH:30]=[C:29](B(O)O)[CH:28]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:26][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:29]3[CH:28]=[N:27][CH:32]=[CH:31][CH:30]=3)[CH:3]=2)[C:8]([CH3:13])([CH3:12])[C:7](=[O:14])[C:6]=1[C:15]([NH:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:16]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 67099310HCID 67099310、化合物

生成物 1

HCID 670992951,1-Dimethylethyl N-((4-hydroxy-1,1-dimethyl-2-oxo-6-(3-pyridinyl)-naphthalen-3-yl)carbonyl)glycinate収率 40%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
150 °C

実験手順

A suspension of 1,1-dimethylethyl N-((6-bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalen-3-yl)carbonyl)glycinate (284 mg, 669 μmol, see Example 39), pyridin-3-ylboronic acid (165 mg, 1339 μmol), and Na2CO3 (2.0M aqueous solution (669 μL, 1339 μmol)) in 1,4-dioxane (5 mL) was treated with Pd(PPh3)4 (77 mg, 67 μmol) in a microwave vial. The vessel was capped, degassed, backfilled with argon (2×), and heated at 150° C. in a microwave for 1200 sec. The reaction was diluted with EtOAc (50 mL), washed with water (50 mL) and brine (50 mL), dried over MgSO4, concentrated in vacuo, and purified by silica gel chromatography (eluant: 20-28-40% EtOAc/hexane) affording 113 mg of the title compound. MS m/e=423.2 (M+H)+.

後処理

  1. customThe vessel was capped
  2. customdegassed
  3. additionThe reaction was diluted with EtOAc (50 mL)
  4. washwashed with water (50 mL) and brine (50 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. custompurified by silica gel chromatography (eluant: 20-28-40% EtOAc/hexane)

出典と根拠

ORDレコード
ord-25a4ea526ba2493d8e4df85b0f24e620
出典データセット
uspto-grants-2011_04
特許番号
US07928139B2

反応ノート

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