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

HRID 1868640노트

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HRID 1868640 반응식
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]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 67099310HCID 67099310, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

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온도
150 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-83dd4732357848b38398a5d7d179175d
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07635715B2

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