4-Fluorophenylboronic acid → (R,R)-N-[4-bromo-3-(4-fluorophenyl)isothiazol-5-yl]-2-methylcyclopropane-carboxamide

HRID 2422716Notes

Reaction equation

HRID 2422716 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:12]1[C:16]([Br:17])=[C:15]([NH:18][C:19]([C@@H:21]2[CH2:23][C@H:22]2[CH3:24])=[O:20])[S:14][N:13]=1>>[Br:17][C:16]1[C:12]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[N:13][S:14][C:15]=1[NH:18][C:19]([C@@H:21]1[CH2:23][C@H:22]1[CH3:24])=[O:20]

Participants

3

Reactant 2

HCID 2856454-Fluorophenylboronic acidHCID 67103560(R,R)-N-[3,4-dibromoisothiazol-5-yl]-2-methylcyclopropanecarboxamide

Product 1

HCID 67180226(R,R)-N-[4-bromo-3-(4-fluorophenyl)isothiazol-5-yl]-2-methylcyclopropane-carboxamide

Conditions

Temperature
70 °C

Procedure

Using a similar procedure to that of Preparation VI-3, but using 1.3 equivalents of 4-fluorophenylboronic acid to 1 equivalent of (R,R)—N-[3,4-dibromoisothiazol-5-yl]-2-methylcyclopropanecarboxamide and stirring the reaction mixture at 70° C. for 1 day affords (R,R)—N-[4-bromo-3-(4-fluorophenyl)isothiazol-5-yl]-2-methylcyclopropane-carboxamide. ES-MS: m/e 357.0 (m+1).

Workup

  1. customof Preparation VI-3

Sources & evidence

ORD record
ord-bc1cbfc598e64fbbae194e3dc7add928
Source dataset
uspto-grants-2011_06
Patent number
US07960419B2

Reaction notes

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