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Dimethylformamide → HCID 178480019, compound

HRID 2358263
Notes
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Reaction equation

HRID 2358263 reaction equation
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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 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

Product 1

HCID 178480019HCID 178480019, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent2×

Conditions

Temperature
130 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2f72b21ebe8c49cfa4eb6fe587a70156
Source dataset
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07763634B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes