Triethylamine → HCID 59375380, compound

HRID 2192983Notes

Reaction equation

HRID 2192983 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6]([NH:16][CH2:17][CH3:18])=[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.[C:21]([NH2:25])(=[O:24])[C:22]#[CH:23].C(N(CC)CC)C>CN(C=O)C.C(Cl)Cl.[Cu]I.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6]([NH:16][CH2:17][CH3:18])=[N:7][C:8]3[C:9]([C:23]#[C:22][C:21]([NH2:25])=[O:24])=[CH:10][NH:11][C:12](=[O:14])[C:13]=3[C:4]=2[CH:3]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 101445PropynamideHCID 59375599HCID 59375599, compound

Product 1

HCID 59375380HCID 59375380, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 9-bromo-6-(ethylamino)-4-iodobenzo[c]-1,6-naphthyridin-1(2H)-one (2.5 g, 5.63 mmol) in DMF at room temperature (49.3 ml) was added propiolamide (583 mg, 8.44 mmol), Copper (I) Iodide (161 mg, 0.844 mmol), triethylamine (1.569 ml, 11.26 mmol), and tetrakis(triphenylphosphine) palladium (651 mg, 0.563 mmol). The flask was put under a blanket of argon, sealed and allowed to stir overnight. The next day the reaction was diluted with 100 ml of DCM, which caused the product to precipitate out of solution. The precipitate was collected by filtration, washed with 50 ml of DCM and dried in vacuo to give the product, 3-[9-bromo-6-(ethylamino)-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-4-yl]prop-2-ynamide. 1H NMR (600 MHz, DMSO-D6) δ 11.76 (br s, 1H), 10.00 (s, 1H), 8.40 (t, 1H), 8.27 (d, 1H), 7.79-7.76, (m, 3H), 7.47 (s, 1H), 3.66 (m, 2H), 1.25 (t, 3H). LRMS (ESI) calc'd for (C17H13BrN4O2) [M+H]+, 385.0; found 385.0.

Workup

  1. customsealed
  2. customto precipitate out of solution
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with 50 ml of DCM
  5. customdried in vacuo

Sources & evidence

ORD record
ord-cb346c955f424e5fa7baf589041a48a1
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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