1-Bromo-2,6-difluorobenzene → HCID 11974837, compound

HRID 1371597Notes

Reaction equation

HRID 1371597 reaction equation
CON(C)[C:4]([C:6]1[C:7]([NH2:15])=[N:8][C:9]([S:12][CH2:13][CH3:14])=[N:10][CH:11]=1)=[O:5].[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:19]=1[Li].BrC1C(F)=CC=CC=1F>>[NH2:15][C:7]1[C:6]([C:4]([C:19]2[C:18]([F:17])=[CH:23][CH:22]=[CH:21][C:20]=2[F:24])=[O:5])=[CH:11][N:10]=[C:9]([S:12][CH2:13][CH3:14])[N:8]=1

Participants

4

Reactant 3

HCID 1235571-Bromo-2,6-difluorobenzeneHCID 119748325-Pyrimidinecarboxamide, 4-amino-2-(ethylthio)-N-methoxy-N-methyl-HCID 178506757HCID 178506757, compound

Product 1

HCID 11974837HCID 11974837, compoundYield 70%

Procedure

The same procedure was used as described in Example 2, starting from 4-amino-2-ethylsulfanyl-pyrimidine-5-carboxylic acid methoxy-methylamide (200 mg, 0.830 mmol, Example 1) and a solution of 2,6-difluorophenyl lithium (˜3 equiv, freshly prepared from 1-bromo-2,6-difluorobenzene (Aldrich), as in Example 2A), to give (4-amino-2-ethylsulfanyl-pyrimidin-5-yl)-(2,6-difluoro-phenyl)-methanone as a white solid (170 mg, 70% yield). HRMS, observed: 296.0667; Calcd for (M+H)+: 296.0664.

Sources & evidence

ORD record
ord-6d47301c7bf84fdf9068291382155aeb
Source dataset
uspto-grants-2007_01
Patent number
US07157455B2

Reaction notes

Loading…