Triethylamine → N-(2-Fluoroethyl)-N′-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea

HRID 1626661Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([NH:17][C:18](=O)[O:19]C2C=CC=CC=2)[CH:5]=[CH:6][C:7]=1[B:8]1[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH3:16])([CH3:15])[O:9]1.C(N(CC)CC)C.Cl.[F:35][CH2:36][CH2:37][NH2:38]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]([NH:38][CH2:37][CH2:36][F:35])=[O:19])[CH:5]=[CH:6][C:7]=1[B:8]1[O:12][C:11]([CH3:13])([CH3:14])[C:10]([CH3:16])([CH3:15])[O:9]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirring solution of phenyl (3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate (intermediate 30) (1.6 g, 4.48 mmol) in dry DMF was added triethylamine (2.03 mL, 14.55 mmol) and 2-fluoroethanamine hydrochloride (2.23 g, 22.40 mmol). The mixture was stirred at 50° C. for 2 h. The solvent was then removed in vacuo affording the title compound which was used without further purification.

Workup

customThe solvent was then removed in vacuo

Sources & evidence

ORD record: ord-18b66467c5ec41f5a39de293b5345980
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785457B2

Reaction notes

Loading…