Dimethylformamide → HCID 11492286, 화합물

HRID 1365070노트

반응식

HRID 1365070 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH2:10][CH2:9][N:8]=[CH:7][C:6]=2[CH:12]=1.[N:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[N:13]1[CH:18]=[CH:17][C:16]([C:2]2[CH:3]=[CH:4][C:5]3[NH:11][CH2:10][CH2:9][N:8]=[CH:7][C:6]=3[CH:12]=2)=[CH:15][CH:14]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 57732439HCID 57732439, 화합물

생성물 1

HCID 11492286HCID 11492286, 화합물

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매

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온도
160 °C

실험 절차

A 20 mL microwave tube was charged 7-bromo-2,3-dihydro-1H-1,4-benzodiazepine (115 mg), 4-pyridylboronic acid (2 equiv), potassium carbonate (2 equiv), dichlorobis(triphenyl-phosphine)palladium(II) (10 mol %), DMF (3.5 mL) and water (0.7 mL) then heated to 160° C. for 360 s using microwave irradiation. The reaction was concentrated to dryness and the residue was taken up in water then extracted with ethyl acetate/tetrahydrofuran (3:1). The organic extracts were combined and dried over sodium sulfate. The drying salts were removed by filtration and the filtrate was concentrated. The residue was triturated with diethyl ether and the resulting solids were collected on filter. Recrystallization from hot tetrahydrofuran provided 7-(4-pyridinyl)-2,3-dihydro-1H-1,4-benzodiazepine as a tan powder (9 mg). H1 NMR (d6-dmso): 8.49 (d, 2H), 8.23 (s, 1H), 7.85 (d, 1H), 7.62 (m, 3H), 7.29 (br t, 1H), 6.80 (d, 1H), 3.85 (m, 2H), 3.25 (m, 2H). Mass (ES+)=224.2 (100%).

후처리

  1. custommicrowave irradiation
  2. concentrationThe reaction was concentrated to dryness
  3. extractionthen extracted with ethyl acetate/tetrahydrofuran (3:1)
  4. dry with materialdried over sodium sulfate
  5. customThe drying salts were removed by filtration
  6. concentrationthe filtrate was concentrated
  7. customThe residue was triturated with diethyl ether
  8. customthe resulting solids were collected
  9. filtrationon filter
  10. customRecrystallization from hot tetrahydrofuran

출처 및 근거

ORD 기록
ord-878759534c9e48b2be7ccc3a95f0f048
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07888503B2

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