Sodium Carbonate → HCID 59264873, 화합물

HRID 646003노트

반응식

HRID 646003 반응식
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:11]=[CH:10]2)(=O)=O.C([O-])([O-])=O.[Na+].[Na+].[Cl:29][C:30]1[CH:35]=[C:34]([O:36][Si](C(C)(C)C)(C)C)[CH:33]=[CH:32][C:31]=1B(O)O>COCCOC.O.CCOC(C)=O.[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:29][C:30]1[CH:35]=[C:34]([OH:36])[CH:33]=[CH:32][C:31]=1[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:11]=[CH:10]2

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 21107087(4-((tert-Butyldimethylsilyl)oxy)-2-chlorophenyl)boronic acidHCID 22622428Methyl 6-(((trifluoromethyl)sulfonyl)oxy)-1-naphthoate

생성물 1

HCID 59264873HCID 59264873, 화합물수율 82%

시약·촉매·용매 4

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of methyl 6-{[(trifluoromethyl)sulfonyl]oxy}-1-naphthoate (0.97 g, 2.91 mmol), tetrakis(triphenylphosphine) palladium (0) (0.13 g, 0.116 mmol), 2 M Na2CO3 (13.6 mL) and 2-chloro-4-[((1,1-dimethylethyl)dimethylsilyl)oxy]phenylboronic acid (1 g, 3.49 mmol) in ethylene glycol dimethyl ether (15.5 mL) was heated at 80° C. for 40 minutes. The reaction mixture was cooled to room temperature, diluted with water and EtOAc, and transferred to a separatory funnel. The organic phase was separated, washed with brine, dried over MgSO4, filtered, and the filtrate was concentrated to give the crude product as an oil. The crude material was purified by flash chromatography over SiO2 with a Hex:EtOAc (0 to 20% EtOAc) gradient to afford 0.74 g (82%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 10.06 (s, 1 H), 8.75 (d, J =9 Hz, 1 H), 8.22 (d, J=8 Hz, 1 H), 8.13 (d, J=7 Hz, 1 H), 8.01 (s, 1 H), 7.68 (m, 1H), 7.61 (t, J=8 Hz, 1 H), 7.34 (d, J=9 Hz, 1 H), 6.96 (m, 1 H), 6.86 (m, 1 H), 3.93 (s, 3 H).

후처리

  1. customtransferred to a separatory funnel
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customto give the crude product as an oil
  8. customThe crude material was purified by flash chromatography over SiO2 with a Hex

출처 및 근거

ORD 기록
ord-6dcc2656e02b47b59dcbe6f51a2cb087
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07705028B2

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