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Diisopropylethylamine → HCID 57609249, 화합물

HRID 546797
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HRID 546797 반응식
Br[C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([N:10]2[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]2)=[CH:4][CH:3]=1.[C:16]([NH:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])(=[O:19])[CH:17]=[CH2:18].C(N(CC)C(C)C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.CN(C=O)C>[CH3:9][O:8][C:6]1[N:7]=[C:2](/[CH:18]=[CH:17]/[C:16]([NH:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:19])[CH:3]=[CH:4][C:5]=1[N:10]1[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]1
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참가 물질

7

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HCID 81531DiisopropylethylamineHCID 20458507tert-Butyl 2-acryloylhydrazinecarboxylateHCID 576093006-bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine

생성물 1

HCID 57609249HCID 57609249, 화합물수율 87.2%

시약·촉매·용매 3

HCID 80271Tri-o-tolylphosphine촉매
HCID 167845
palladium(II) acetate
촉매
HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

DMF (52 mL) was added to the 6-Bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine (13.0 g, 48.5 mmol) and the tert-Butyl 2-acryloylhydrazinecarboxylate (9.9 g, 53.3 mmol) at room temperature under nitrogen atmosphere, And the mixture was stirred at 50° C. for 10 minutes. Tri(o-tolyl)phosphine (885 mg, 2.90 mmol), Palladium (II) acetate (327 mg, 1.45 mmol) and N,N-diisopropylethylamine (12.7 mL, 72.7 mmol) were added to the mixture, and the reaction mixture was stirred at 100° C. for 4 hours. The reaction mixture was cooled to room temperature and filtrated through Celite. The residue was washed twice with DMF (6 mL). Water (104 mL) was added dropwise to the filtrate at room temperature over 10 minutes. The mixture was stirred at room temperature for 15 hours. After the mixture was filtrated, the residue was washed with water/DMF=2:1 (30 mL) and MTBE (30 mL). The obtained solid was suspended in MTBE (50 mL) at room temperature for 2 hours, filtrated and dried under the reduced pressure to obtain the title compound (15.8 g, 87% yield).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltrated through Celite
  3. washThe residue was washed twice with DMF (6 mL)
  4. additionWater (104 mL) was added dropwise to the filtrate at room temperature over 10 minutes
  5. stirringThe mixture was stirred at room temperature for 15 hours
  6. filtrationAfter the mixture was filtrated
  7. washthe residue was washed with water/DMF=2:1 (30 mL) and MTBE (30 mL)
  8. waitThe obtained solid was suspended in MTBE (50 mL) at room temperature for 2 hours
  9. filtrationfiltrated
  10. customdried under the reduced pressure

출처 및 근거

ORD 기록
ord-941464c36edb49b58f5ca6e1aa52bdb0
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07935815B2

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