Potassium Carbonate → 6-(4-Bromo-3-formyl-phenoxy)-2-tert-butylamino-nicotinonitrile

HRID 1471596Notes

Reaction equation

[C:1]([NH:5][C:6]1[N:13]=[C:12](Cl)[CH:11]=[CH:10][C:7]=1[C:8]#[N:9])([CH3:4])([CH3:3])[CH3:2].[Br:15][C:16]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][C:17]=1[CH:18]=[O:19].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:15][C:16]1[CH:23]=[CH:22][C:21]([O:24][C:12]2[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])[N:13]=2)=[CH:20][C:17]=1[CH:18]=[O:19]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-tert-butylamino-6-chloro-nicotinonitrile (4, 630 mg, 3 mmol) in DMF (100 mL) were added 2-bromo-5-hydroxy-benzaldehyde (603 mg, 3 mmol) and K2CO3 (828 mg, 6 mmol). The reaction was heated at 80° C. for 24 h. After cooling to r.t., DMF was removed in vacuo. Purification was accomplished by Biotage silica gel chromatography with a 2.5%-10% EtOAc/hexanes gradient to afford 950 mg (85% yield) of the title compound.

Workup

temperatureAfter cooling to r.t.
customDMF was removed in vacuo
customPurification

Sources & evidence

ORD record: ord-8316ef0f2dd14eccbcdfeaa34563b5bc
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012431B2

Reaction notes

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