Sodium Carbonate → HCID 90411390、化合物

HRID 2175945ノート

反応式

HRID 2175945 の反応式
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].[CH3:15][N:16]1[C:20](B2OC(C)(C)C(C)(C)O2)=[C:19]([CH3:30])[CH:18]=[N:17]1.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>[CH3:15][N:16]1[C:20]([C:2]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:19]([CH3:30])[CH:18]=[N:17]1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 46311273Ethyl 2-bromo-6-methoxybenzoateHCID 578266761,4-dimethyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

生成物 1

HCID 90411390HCID 90411390、化合物収率 95.2%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
100 °C

実験手順

In a microwave vial was dissolved ethyl 2-bromo-6-methoxybenzoate (500 mg, 1.54 mmol) and 1,4-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (377 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 (402 mg, 95%). MS (ESI) mass calcd. for C15H18N2O3, 274.1; m/z found 275.2 [M+H]+. 1H NMR (400 MHz, Chloroform-d) 7.45 (dd, J=8.4, 7.6 Hz, 1H), 7.29 (s, 1H), 7.04 (dd, J=8.5, 0.9 Hz, 1H), 6.84 (dd, J=7.6, 0.9 Hz, 1H), 4.07 (qd, J=7.2, 1.5 Hz, 2H), 3.90 (s, 3H), 3.61 (s, 3H), 1.86 (s, 3H), 1.01 (t, J=7.1 Hz, 3H).

後処理

  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)

出典と根拠

ORDレコード
ord-b93ddc4577a34e5fbfec4ab884b79ef5
出典データセット
uspto-grants-2015_06
特許番号
US09062078B2

反応ノート

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