HCID 57786168, 화합물 → HCID 57786038, 화합물

HRID 1628916노트

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HRID 1628916 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:25]=[O:26])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:15]3[C:20]([Br:21])=[CH:19][C:18]([O:22][CH3:23])=[CH:17][C:16]=3[Br:24])[CH2:12][CH2:13][CH2:14][N:7]21.[CH2:27]([Mg]Br)[CH3:28]>O1CCCC1.[Cl-].[NH4+]>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[C:16]([Br:24])=[CH:17][C:18]([O:22][CH3:23])=[CH:19][C:20]=4[Br:21])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH:25]([OH:26])[CH2:27][CH3:28])=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 57786168HCID 57786168, 화합물HCID 178418443HCID 178418443, 화합물

생성물 1

HCID 57786038HCID 57786038, 화합물수율 92%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 25517Ammonium Chloride용매

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온도
0 °C

실험 절차

To a solution of 9-chloro-1-(2,6-dibromo-4-methoxyphenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carbaldehyde (80.0 mg, 0.160 mmol) in tetrahydrofuran (3.2 mL) was added dropwise ethylmagnesium bromide (3 M solution in diethyl ether, 0.107 mL, 0.321 mmol) at 0° C., and the mixture was stirred at 0° C. for 5 min. The reaction mixture was diluted with aqueous saturated ammonium chloride, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture to give the title compound as a colorless solid (78.0 mg, 0.147 mmol, 92%).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture

출처 및 근거

ORD 기록
ord-1782aba9b84d45caab3f507166b85890
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785460B2

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