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Dimethylformamide → HCID 178480019、化合物

HRID 2358263
ノート
印刷プレビュー

反応式

HRID 2358263 の反応式
Br[C:2]1[CH:26]=[CH:25][C:5]2=[C:6]3[N:17]=[C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[Cl:24])[NH:15][C:7]3=[C:8]3[C:13]([C:12](=[O:14])[NH:11][CH:10]=[CH:9]3)=[C:4]2[CH:3]=1.[Cl-].[Li+].[CH3:29][N:30]1[CH:34]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:32]=[N:31]1.CN(C=O)C>C(OCC)(=O)C.C([O-])([O-])=O.[Na+].[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:16]1[NH:15][C:7]2=[C:8]3[C:13](=[C:4]4[CH:3]=[C:2]([C:33]5[CH:32]=[N:31][N:30]([CH3:29])[CH:34]=5)[CH:26]=[CH:25][C:5]4=[C:6]2[N:17]=1)[C:12](=[O:14])[NH:11][CH:10]=[CH:9]3
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 433294Lithium ChlorideHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 1785186779-Bromo-2-(2-chlorophenyl)-3,6-dihydro-7H-benzo[h]imidazo[4,5-f]isoquinolin-7-one

生成物 1

HCID 178480019HCID 178480019、化合物

試薬・触媒・溶媒 3

HCID 178418397
HCID 178418397、化合物
触媒
HCID 8857Ethyl Acetate溶媒
HCID 10340Sodium Carbonate溶媒2 回

反応条件

温度
130 °C

実験手順

9-Bromo-2-(2-chlorophenyl)-3,6-dihydro-7H-benzo[h]imidazo[4,5-f]isoquinolin-7-one (30 mg, 0.071 mmol), lithium chloride (6 mg, 0.14 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (30 mg, 0.14 mmol), and tetrakis(triphenylphosphine)palladium(0) (8 mg, 0.0071 mmol) were placed in a microwave tube. Na2CO3 (2 M, 0.25 mL) and DMF (1 mL) were added and the solution was heated in the microwave at 130° C. for ten minutes. The solution was cooled to ambient temperature diluted with ethyl acetate and Na2CO3 (2 M). The organic layer was separated, washed with brine, dried over MgSO4, filtered and concentrated to dryness. The crude residue was purified on silica gel to afford the title compound. 1H NMR (500 MHz, DMSO-d6, δH) 11.56 (bs, 1 H), 10.49 (bs, 1 H), 8.56-8.45 (m, 1 H), 8.18 (s, 1 H), 7.90-7.87 (m, 3 H), 7.69 (d, 1 H, J=7.2 Hz), 7.58-7.54 (m, 3H), 7.34-7.28 (m, 1 H): [M+1]+ 426.1.

後処理

  1. temperatureThe solution was cooled to ambient temperature
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe crude residue was purified on silica gel

出典と根拠

ORDレコード
ord-2f72b21ebe8c49cfa4eb6fe587a70156
出典データセット
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07763634B2

反応ノート

読み込み中…

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