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Water → 5-Bromo-N-(3,4-dimethoxybenzyl)-2-pyridin-3-ylbenzamide

HRID 1948557
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HRID 1948557 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([CH:21]=1)[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)=[O:8].[N:23]1[CH:28]=[CH:27][CH:26]=[C:25](B2OC(C)(C)C(C)(C)O2)[CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>C1COCC1.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:25]2[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=2)=[C:6]([CH:21]=1)[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)=[O:8]
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참가 물질

8

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27346563-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 45725783HCID 45725783, 화합물

생성물 1

HCID 584084115-Bromo-N-(3,4-dimethoxybenzyl)-2-pyridin-3-ylbenzamide

시약·촉매·용매 3

HCID 178418807
HCID 178418807, 화합물
촉매
HCID 8028Tetrahydrofuran용매
HCID 8857Ethyl Acetate용매

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온도
120 °C

실험 절차

A solution of 1-2 (100 mg, 0.210 mmol, 1.0 equiv) in THF (2 ml) in a microwave vial was treated with pyridine-3-boronic acid pinacol ester (47.4 mg, 0.231 mmol, 1.1 equiv), cesium carbonate (163 mg, 0.500 mmol, 2.4 equiv), PdCl2(dppf)-CH2Cl2 adduct (17.15 mg, 0.021 mmol, 0.1 equiv), and 0.5 mL water. The mixture was heated to 120° C. in a microwave reactor for 10 min. The mixture was cooled to RT and diluted with EtOAc. The mixture was washed with sat. aq. NH4Cl, dried over Na2SO4, filtered and concentrated. The crude material (1-3) was used as is in the next step. ESI+ MS [M+H]+ C21H19BrN2O3: 428.0 found, 427.3 required.

후처리

  1. temperatureThe mixture was cooled to RT
  2. washThe mixture was washed with sat. aq. NH4Cl
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-882cae3045aa497caca54eac90add8d7
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08399494B2

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