Ethylene Glycol → 5-bromo-6-(2-hydroxyethoxy)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

HRID 629091Notes

Reaction equation

[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[CH2:23]([OH:26])[CH2:24][OH:25].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[C:3]([O:25][CH2:24][CH2:23][OH:26])=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 5-bromo-6-chloro-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 44.2, 400 mg, 1.011 mmol), ethane-1,2-diol (1 mL, 17.88 mmol), K2CO3 (210 mg, 1.517 mmol) and DMF (2 mL) was stirred at 50° C. overnight. The solvent was evaporated off under reduced pressure and the residue was treated with water and extracted with DCM. The combined extracts were dried over Na2SO4 and the solvent was evaporated off under reduced pressure to afford the title compound which was used directly. UPLC-MS (Condition 2) tR=1.04 min, m/z=421.3/423.3 [M+H]+.

Workup

customThe solvent was evaporated off under reduced pressure
additionthe residue was treated with water
extractionextracted with DCM
dry with materialThe combined extracts were dried over Na2SO4
customthe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record: ord-d9438c715f824954b33acbd3733b72cd
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315489B2

Reaction notes

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