Triethylamine → 3-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-6-(pyridin-2-yl)-3H-imidazo[4,5-b]pyridin-2-amine

HRID 2178373Notes

Reaction equation

HRID 2178373 reaction equation
I[C:2]1[CH:3]=[C:4]2[N:10]=[C:9](NC(=O)OCC)[N:8]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]4[CH:27]=[N:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=4)=[C:20]([O:34][CH3:35])[CH:19]=3)[C:5]2=[N:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=1)CCC.C([N:57](CC)CC)C>CN(C)C=O.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:35][O:34][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][C:21]=1[O:24][CH2:25][C:26]1[CH:27]=[N:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=1)[CH2:17][N:8]1[C:5]2=[N:6][CH:7]=[C:2]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=3)[CH:3]=[C:4]2[N:10]=[C:9]1[NH2:57]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 6077842-(Tributylstannyl)pyridineHCID 131733017ethyl (6-iodo-3-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-3H-imidazo[4,5-b]pyridin-2-yl)carbamate

Product 1

HCID 1180098243-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-6-(pyridin-2-yl)-3H-imidazo[4,5-b]pyridin-2-amineYield 13%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of ethyl (6-iodo-3-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzyl)-3H-imidazo[4,5-b]pyridin-2-yl)carbamate (0.250 g, 0.42 mmol), 2-(tributylstannyl)pyridine (0.235 g, 0.63 mmol), copper(I) iodide (0.040 g, 0.21 mmol) and triethylamine (0.130 g, 1.26 mmol) in N,N-dimethylformamide (5 mL) was added bis(triphenylphosphine)palladium(II) dichloride (0.018 g, 0.042 mmol). The mixture was irradiated in a microwave reactor at 140° C. After 1.5 h, the mixture was allowed to cool to room temperature and was filtered through Celite. The filtrate was concentrated. The residue was purified by prep-HPLC to afford 0.025 g (13%) of the product as a white solid: 1H NMR (500 MHz, DMSO-d6) δ 8.64 (d, J=4.0 Hz, 1H), 8.62 (d, J=2.0 Hz, 1H), 8.20 (d, J=2.5 Hz, 1H), 8.06 (d, J=2.0 Hz, 1H), 7.97 (d, J=7.5 Hz, 1H), 7.84-7.76 (m, 1H), 7.74-7.72 (m, 1H), 7.32-7.29 (m, 1H), 7.12 (d, J=6.0 Hz, 1H), 7.00-6.77 (m, 3H), 6.82 (d, J=8.5 Hz, 1H), 6.83-6.74 (m, 1H), 5.24 (s, 2H), 4.96 (s, 2H), 3.83 (s, 3H), 3.70 (s, 3H) ppm; (M+1)=469.

Workup

  1. customThe mixture was irradiated in a microwave reactor at 140° C
  2. filtrationwas filtered through Celite
  3. concentrationThe filtrate was concentrated
  4. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-e9149112f3274e48b959cf82c9eae0bc
Source dataset
uspto-grants-2015_06
Patent number
US09067914B1

Reaction notes

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