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(2,4-Dimethylphenyl)boronic acid → 2-(2,4-Dimethylphenyl)-N,N-dipropylimidazo[1,2-a]pyridin-5-amine

HRID 2235542
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HRID 2235542 반응식
Br[C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([N:10]([CH2:14][CH2:15][CH3:16])[CH2:11][CH2:12][CH3:13])[N:5]2[CH:17]=1.[CH3:18][C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=1B(O)O.CC([O-])(C)C.[K+]>COCCOC.CC(O)(C)C.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>[CH3:18][C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=1[C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([N:10]([CH2:14][CH2:15][CH3:16])[CH2:11][CH2:12][CH3:13])[N:5]2[CH:17]=1
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참가 물질

7

반응물 3

HCID 4198739(2,4-Dimethylphenyl)boronic acidHCID 23665647Potassium tert-butoxideHCID 685819902-Bromo-N,N-dipropylimidazo[1,2-a]pyridin-5-amine

생성물 1

HCID 588964632-(2,4-Dimethylphenyl)-N,N-dipropylimidazo[1,2-a]pyridin-5-amine수율 2%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물
촉매
HCID 6386tert-Butanol용매
HCID 80711,2-Dimethoxyethane용매2회

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온도
50 °C

실험 절차

2-Bromo-N,N-dipropylimidazo[1,2-a]pyridin-5-amine (prepared in example 61) (0.17 g, 0.57 mmol) was dissolved in 1,2-dimethoxyethane (DME) (1.5 mL). Pd(PPh3)4 (0.033 g, 0.028 mmol) was added and the reaction was stirred at 50° C. for 15 minutes. The solution was cooled and 2,4-dimethylphenylboronic acid (0.103 g, 0.69 mmol) in DME (1 mL) was added to the reaction mixture. KOtBu (0.128 g, 1.14 mmol) in tBuOH (1 mL) was also added to the reaction. The reaction was heated to 100° C. for 1 hr. The solution was filtered through paper and concentrated. Crude material was purified via reverse phase HPLC (acetonitrile containing 0.1% TFA/water containing 0.1% TFA) to obtain 3.1 mg of the title compound (2% yield).

후처리

  1. temperatureThe solution was cooled
  2. temperatureThe reaction was heated to 100° C. for 1 hr
  3. filtrationThe solution was filtered through paper
  4. concentrationconcentrated
  5. customCrude material was purified via reverse phase HPLC (acetonitrile containing 0.1% TFA/water containing 0.1% TFA)

출처 및 근거

ORD 기록
ord-69501b768d5d4a489bb84aaecbbae6a8
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07714009B2

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