Sodium Carbonate → HCID 90414470, 화합물

HRID 869020노트

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HRID 869020 반응식
Br[C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].CC1(C)C(C)(C)OB([C:23]2[NH:27][N:26]=[CH:25][CH:24]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.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>[CH3:14][O:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:2]([C:23]2[NH:27][N:26]=[CH:25][CH:24]=2)[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 219315393-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 46311273Ethyl 2-bromo-6-methoxybenzoate

생성물 1

HCID 90414470HCID 90414470, 화합물수율 33%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

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온도
100 °C

실험 절차

In a microwave vial was dissolved ethyl 2-bromo-6-methoxybenzoate (500 mg, 1.54 mmol) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (330 mg, 1.70 mmol) in DME (10 mL) and water (2 mL). Na2CO3 (259 mg, 3.09 mmol) was then added followed by Pd(PPh3)4 (89 mg, 0.077 mmol) and the reaction mixture was degassed with N2 for 10 minutes. The reaction mixture was then heated at 100° C. for 1 h in the microwave. The mixture was cooled to room temperature, filtered through Celite and washed with EtOAc and DCM. The crude solution was concentrated in vacuo and directly purified via silica gel chromatography (10-80% EtOAc in hexanes) to afford the title compound (125 mg, 33%). MS (ESI) mass calcd. for C13H14N2O3, 246.3. m/z found 247.1 [M+H]+. 1H NMR (400 MHz, Chloroform-d) δ 7.63 (d, J=2.2 Hz, 1H), 7.44-7.37 (m, 1H), 7.24 (d, J=8.1 Hz, 1H), 6.94 (dd, J=8.3, 0.9 Hz, 1H), 6.53 (d, J=2.3 Hz, 1H), 4.29 (q, J=7.2 Hz, 2H), 3.88 (s, 3H), 1.25-1.16 (m, 3H).

후처리

  1. customthe reaction mixture was degassed with N2 for 10 minutes
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered through Celite
  4. washwashed with EtOAc and DCM
  5. concentrationThe crude solution was concentrated in vacuo
  6. customdirectly purified via silica gel chromatography (10-80% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-18568fb50e0a4594b68d9f0d7fddf865
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969352B2

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