Potassium Carbonate → 6-(4-Bromo-3-formyl-phenoxy)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethylamino]-nicotinonitrile

HRID 1471602Notes

Reaction equation

[C:1]([Si:5]([CH3:20])([CH3:19])[O:6][CH2:7][CH2:8][NH:9][C:10]1[N:17]=[C:16](Cl)[CH:15]=[CH:14][C:11]=1[C:12]#[N:13])([CH3:4])([CH3:3])[CH3:2].[Br:21][C:22]1[CH:41]=[CH:40][C:25]([O:26]C2C=CC(C#N)=C(OCC(F)F)N=2)=[CH:24][C:23]=1[CH:42]=[O:43].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:21][C:22]1[CH:41]=[CH:40][C:25]([O:26][C:16]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([NH:9][CH2:8][CH2:7][O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:20])[CH3:19])[N:17]=2)=[CH:24][C:23]=1[CH:42]=[O:43]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-[2-(tert-butyl-dimethyl-silanyloxy)-ethylamino]-6-chloro-nicotinonitrile (4, 1.1 g, 3.5 mmol) in DMF (80 mL) were added 2-bromo-5-hydroxy-benzaldehyde (5, 0.75 g, 3.7 mmol) and K2CO3 (0.97 g, 7.05 mmol). The reaction was heated at 80° C. for 24 h. The DMF was removed in vacuo. Purification was accomplished by Biotage silica gel chromatography with 1%-3% EtOAc/hexanes gradient to afford 1.26 g (75% yield) of the title compound.

Workup

customThe DMF was removed in vacuo
customPurification

Sources & evidence

ORD record: ord-40df7d4bf40e420984cc6796d4cc8e00
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012431B2

Reaction notes

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