Triethylamine → tert-butyl-N-[5-amino-6-(2-phenylethynyl)pyridin-2-yl]carbamate

HRID 535386Notes

Reaction equation

[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[C:10](Br)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)#[CH:18].C(N(CC)CC)C>C(#N)C.C1COCC1.[Cu]I.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].Cl[Pd]Cl>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[C:10]([C:18]#[C:17][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 45 °C

Procedure

Tert-butyl-N-(5-amino-6-bromopyridin-2-yl)carbamate A5 (617 mg, 1.82 mmol), ethynylbenzene (420 μl, 3.82 mmol), copper(I) iodide (35 mg, 0.18 mmol), 1,1′-Bis-(diphenylphosphino)ferrocene]dichloropalladium(II) (66.4 mg, 0.09 mmol) and triethylamine (631 μl, 4.55 mmol) are stirred under argon atmosphere in a mixture of ACN (10 ml) and THF (5 ml) for 2 h at RT. The mixture is warmed to 45° C. and stirred for 70 h. The mixture is concentrated in vacuo and the product purified by RP HPLC. Yield: 320 mg (57%). HPLC-MS: M+H=310; tR=2.05 min (*Method—2).

Workup

concentrationThe mixture is concentrated in vacuo
customthe product purified by RP HPLC

Sources & evidence

ORD record: ord-41680f1deecf4ff5878dca69f376f10a
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859541B2

Reaction notes

Loading…