Sodium Carbonate → 5-(2-fluorophenyl)-7-(4-pyridinyl)-2,3-dihydro-1H-1,4-benzodiazepine

HRID 1365058노트

반응식

HRID 1365058 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH2:10][CH2:9][N:8]=[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[F:18])[C:6]=2[CH:19]=1.[N:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.CN(C)C=O>[F:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:7]1[C:6]2[CH:19]=[C:2]([C:23]3[CH:24]=[CH:25][N:20]=[CH:21][CH:22]=3)[CH:3]=[CH:4][C:5]=2[NH:11][CH2:10][CH2:9][N:8]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 577324247-bromo-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine

생성물 1

HCID 115587405-(2-fluorophenyl)-7-(4-pyridinyl)-2,3-dihydro-1H-1,4-benzodiazepine수율 41.4%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

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온도
150 °C

실험 절차

A 5-mL microwave tube was charged with 7-bromo-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine (85 mg), 4-pyridylboronic acid (100 mg), dichlorobis(triphenylphosphine)palladium(II) (20 mg), dimethylformamide (3.5 mL) and a saturated solution of sodium carbonate (0.5 mL). The reaction was heated to 150° C. for 360 seconds using microwave irradiation. The reaction was concentrated to dryness and the residue was taken up in water and extracted with ethyl acetate. The organic extracts were combined and dried over magnesium sulfate. The drying agent was filtered and the filtrate was concentrated to an oil. Silica gel purification provided the title compound (5-(2-fluorophenyl)-7-(4-pyridinyl)-2,3-dihydro-1H-1,4-benzodiazepine, 35 mg) as an off-white crystalline solid. H1 NMR (d6-dmso): 8.40 (d, 2H), 7.57 (dd, 1H), 7.44 (t, 2H), 7.25 (m, 3H), 7.18 (m, 1H), 7.12 (m, 1H), 6.99 (br t, 1H), 6.85 (d, 1H), 3.98 (m, 2H), 3.54 (m, 2H). Mass (ES+)=318.2 (100%).

후처리

  1. custommicrowave irradiation
  2. concentrationThe reaction was concentrated to dryness
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe drying agent was filtered
  6. concentrationthe filtrate was concentrated to an oil
  7. customSilica gel purification

출처 및 근거

ORD 기록
ord-9394e1a7f11a4ed794c72981fa589c9d
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07888503B2

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