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Dimethylformamide → HCID 178480019, 화합물

HRID 2358263
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HRID 2358263 반응식
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
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참가 물질

8

반응물 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

생성물 1

HCID 178480019HCID 178480019, 화합물

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 8857Ethyl Acetate용매
HCID 10340Sodium Carbonate용매2회

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온도
130 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2f72b21ebe8c49cfa4eb6fe587a70156
출처 데이터셋
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07763634B2

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