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Sodium Carbonate → 3-Benzo[1,3]dioxol-5-yl-2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole

HRID 8245
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HRID 8245 반응식
Br[C:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[N:8]=2)=[N:5][N:4]2[CH2:14][CH2:15][CH2:16][C:3]=12.[CH2:17]1[O:25][C:24]2[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][C:19]=2[O:18]1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.CO.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>[O:18]1[C:19]2[CH:20]=[CH:21][C:22]([C:2]3[C:6]([C:7]4[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[N:8]=4)=[N:5][N:4]4[CH2:14][CH2:15][CH2:16][C:3]=34)=[CH:23][C:24]=2[O:25][CH2:17]1
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참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 99002873-bromo-2-(6-methylpyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole

생성물 1

HCID 99230303-Benzo[1,3]dioxol-5-yl-2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 887Methanol용매
HCID 1140Toluene용매

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온도
80 °C

실험 절차

A mixture of 3-bromo-2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole (99 mg, 0.36 mmol), 3,4-methylenedioxyphenylboronic acid (65 mg, 0.39 mmol), (PPh3)4Pd (20 mg, 0.02 mmol), 1 N aqueous sodium carbonate solution (500 μL, 0.5 mmol) in toluene (5 mL) and methanol (1 mL) is purged with argon for 10 min and heated at 80° C. under nitrogen for 30 h. The mixture is cooled and partitioned between water and ethyl acetate, and the organic portion washed with water and brine, dried (sodium sulfate), filtered, and concentrated in vacuo. The crude residue is chromatographed on SiO2 (ethyl acetate) to yield the title compound, 10 mg (9%), as a yellow solid.

후처리

  1. customis purged with argon for 10 min
  2. temperatureThe mixture is cooled
  3. custompartitioned between water and ethyl acetate
  4. washthe organic portion washed with water and brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue is chromatographed on SiO2 (ethyl acetate)

출처 및 근거

ORD 기록
ord-07ff4df06c1946268840014ad806ef34
출처 데이터셋
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07087626B2

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