2-(Tributylstannyl)pyridine → (1H-Indol-5-yl)-(2-pyridin-2-yl-thieno[3,2-b]pyridin-7-yl)-amine

HRID 2297806Notes

Reaction equation

Br[C:2]1[S:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2[NH:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][CH:16]=[CH:15]3)[CH:3]=1.C([Sn](CCCC)(CCCC)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)CCC>CN(C)C=O.[Cu](I)I.[CH2-]C1C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd+]>[NH:17]1[C:18]2[C:14](=[CH:13][C:12]([NH:11][C:8]3[CH:7]=[CH:6][N:5]=[C:4]4[CH:3]=[C:2]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=5)[S:10][C:9]=34)=[CH:20][CH:19]=2)[CH:15]=[CH:16]1

Participants

Conditions

Temperature: 90 °C

Procedure

In a sealed tube (2-bromo-thieno[3,2-b]pyridin-7-yl)-(1H-indol-5-yl)-amine (150 mg, 0.29 mmol) and 2-(tributylstannyl)pyridine (118 mg, 1.1 mmol) were combined in 3 mL of dimethylformamide along with copper iodide (3 mg, 0.015 mmol). Nitrogen was bubbled through the solution and trans-benzyl(chloro)bis-(triphenylphosphine)palladium(II) (33 mg, 0.044 mmol) was added, the tube was sealed and heated to 90° C. After 14 hours the solution was cooled and concentrated to dryness. Chromatography on 15 g of silica gel with CH2Cl2/MeOH (5-20%) afforded 30.3 mg (28%) of,the title compound. LC-MS: 343 (MH+); HPLC RT: 3.94 minutes.

Workup

additionwas added
customthe tube was sealed
temperatureAfter 14 hours the solution was cooled
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-d5c9c266044a481bbedc84023dda0685
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492383B1

Reaction notes

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