Tetrahydrofuran → 4-Bromo-6-[2-[tris(propan-2-yl)silyl]ethynyl}pyridin-2-amine

HRID 923659Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4](Br)[N:3]=1.[C:10]([Si:12]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14])#[CH:11].C(N(CC)CC)C.C1COCC1>C(#N)C.O.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.[Cu]I>[Br:8][C:6]1[CH:5]=[C:4]([C:11]#[C:10][Si:12]([CH:13]([CH3:15])[CH3:14])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])[N:3]=[C:2]([NH2:1])[CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Under argon atmosphere dichlorobis(triphenylphosphine)palladium(II) (1.6 g, 2.2 mmol) is added to a mixture of 2-amino-4,6-dibromopyridine (5.44 g, 21.6 mmol), ethynyl-tri(propan-2-yl)silane (5.1 g, 28.1 mmol), copper(I) iodide (0.44 g, 2.3 mmol) and triethylamine (9 ml, 64 mmol) in ACN (32 ml) with THF (16 ml). After stirring at 50° C. for 17 h the mixture is diluted with water and extracted with EtOAc. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is purified by NP chromatography. Yield: 4.7 g (62%). HPLC-MS: M+H=353/355; tR=1.80 min (METHOD—1).

Workup

extractionextracted with EtOAc
dry with materialThe combined organic layers are dried over MgSO4
concentrationconcentrated in vacuo
customThe product is purified by NP chromatography

Sources & evidence

ORD record: ord-c8c290959038463abdda31a65883c50f
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278978B2

Reaction notes

Loading…