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Triethylamine → 2-(1-biphenyl-3-yl-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl)benzonitrile

HRID 1616247
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HRID 1616247 반응식
[CH3:1][N:2]1[C:6]2=[N:7][C:8]([C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[C:13]#[N:14])=[CH:9][CH:10]=[C:5]2[NH:4][C:3]1=[O:19].[C:20]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:25]=[CH:24][CH:23]=[C:22](B(O)O)[CH:21]=1.C(N(CC)CC)C>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:20]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:25]=[CH:24][CH:23]=[C:22]([N:4]2[C:5]3[C:6](=[N:7][C:8]([C:11]4[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=4[C:13]#[N:14])=[CH:9][CH:10]=3)[N:2]([CH3:1])[C:3]2=[O:19])[CH:21]=1
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참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 2734315(3-Phenylphenyl)boronic acidHCID 866918212-(3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl)benzonitrile

생성물 1

HCID 866918592-(1-biphenyl-3-yl-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl)benzonitrile

시약·촉매·용매 2

HCID 8895Cupric acetate촉매
HCID 6344
Dichloromethane
용매
2회

실험 절차

To a solution of 4-1 (13 mg, 0.052 mmol) in DCM (0.25 mL) was added copper (II) acetate, biphenyl-3-ylboronic acid (30 mg, 0.16 mmol) and triethylamine (0.022 mL, 16 mg, 0.16 mmol) at room temperature. After 4 days, the crude mixture was diluted in DCM (4 mL), filtered, concentrated and purified via reverse phase chromatography (1-100% Acetonitrile, 0.1% TFA in H2O) and the desired fractions were concentrated to give 76-1. MS (M+H)+: observed=403.0, calculated=403.2.

후처리

  1. filtrationfiltered
  2. concentrationconcentrated
  3. custompurified via reverse phase chromatography (1-100% Acetonitrile, 0.1% TFA in H2O)
  4. concentrationthe desired fractions were concentrated
  5. customto give 76-1

출처 및 근거

ORD 기록
ord-8869f156541a4f3e9705e8b746cd9994
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08765784B2

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