Diisopropylamine → HCID 59375684, compound

HRID 2192984Notes

Reaction equation

HRID 2192984 reaction equation
[Br:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6]([NH:16][CH:17]([CH3:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[N:7][C:8]3[C:9](I)=[CH:10][NH:11][C:12](=[O:14])[C:13]=3[C:4]=2[CH:3]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.C(NC(C)C)(C)C.[CH:48]1([C:51]#[CH:52])[CH2:50][CH2:49]1>[Cu]I.C(OCC)(=O)C>[Br:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6]([NH:16][CH:17]([CH3:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[N:7][C:8]3[C:9]([C:52]#[C:51][CH:48]4[CH2:50][CH2:49]4)=[CH:10][NH:11][C:12](=[O:14])[C:13]=3[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 138823CyclopropylacetyleneHCID 521585Tris(furan-2-yl)phosphaneHCID 59375664HCID 59375664, compound

Product 1

HCID 59375684HCID 59375684, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

9-bromo-4-iodo-6-[(1,2,2-trimethylpropyl)amino]benzo[c]-1,6-naphthyridin-1(2H)-one (5.03 g, 10.06 mmol), copper(I) iodide (0.230 g, 1.207 mmol), Pd(allyl)Cl dimer (0.221 g, 0.603 mmol) and tri(2-furyl)phosphine (0.280 g, 1.207 mmol) were combined in a 10-dram vial that was then flushed with nitrogen and kept under a nitrogen atmosphere. MeCN (101 ml) was then added followed by diisopropylamine (4.30 ml, 30.2 mmol) and cyclopropylacetylene (2.57 ml, 30.2 mmol). The resulting solution was then heated to 45° C. and stirred in the dark for 30 min. Then, the reaction was poured into ethyl acetate (350 mL) and washed with sat NaHCO3, water, brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting oil was purified by column chromatography on silica gel, eluting with EtOAc/Hexanes to afford the title compound as a pale yellow solid. LRMS (ESI) calc'd for (C23H25BrN3O) [M+H]+, 438.1; found 438.0.

Workup

  1. customwas then flushed with nitrogen
  2. additionMeCN (101 ml) was then added
  3. washwashed
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting oil was purified by column chromatography on silica gel
  8. washeluting with EtOAc/Hexanes

Sources & evidence

ORD record
ord-44864404b8a64defaef748c6a66ee5cc
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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