Dimethylformamide → HCID 11492286、化合物

HRID 1365070ノート

反応式

HRID 1365070 の反応式
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

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 57732439HCID 57732439、化合物

生成物 1

HCID 11492286HCID 11492286、化合物

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒

反応条件

温度
160 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-878759534c9e48b2be7ccc3a95f0f048
出典データセット
uspto-grants-2011_02
特許番号
US07888503B2

反応ノート

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