1-(2-Bromo-4-methylsulfonylphenoxy)-2,4-difluorobenzene → US10023592, Example 120

HRID 575607Notes

Reaction equation

HRID 575607 reaction equation
[F:1][C:2]1[C:3](=[O:18])[N:4]([CH3:17])[CH:5]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:7]=1.Br[C:20]1[CH:34]=[C:33]([S:35]([CH3:38])(=[O:37])=[O:36])[CH:32]=[CH:31][C:21]=1[O:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[F:30]>O1CCOCC1.C(=O)(O)[O-].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:30][C:24]1[CH:25]=[C:26]([F:29])[CH:27]=[CH:28][C:23]=1[O:22][C:21]1[CH:31]=[CH:32][C:33]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:34][C:20]=1[C:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:18])[N:4]([CH3:17])[CH:5]=1

Participants

6

Reactant 2

HCID 1180221721-(2-Bromo-4-methylsulfonylphenoxy)-2,4-difluorobenzeneHCID 1238237903-Fluoro-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one

Product 1

HCID 118021856US10023592, Example 120Yield 46%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 769Bicarbonate IonSolventHCID 312751,4-DioxaneSolvent

Procedure

The title compound of Example 119, step 2 (40 mg, 0.16 mmol), 1-(2-bromo-4-methylsulfonylphenoxy)-2,4-difluorobenzene (58 mg, 0.16 mmol) and Pd(dppf)Cl2 (12 mg, 10%) in 1,4-dioxane (880 μL) and saturated bicarbonate solution (aq) (220 μL) were reacted, worked up and purified in a manner similar to Example 117. The title compound (26 mg, 46%) was obtained as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ 3.25 (s, 3H) 3.60 (s, 3H) 6.91-6.99 (m, 1H) 7.16-7.30 (m, 1H) 7.49-7.62 (m, 2H) 7.76-7.86 (m, 2H) 8.00 (m, 2H) LCMS (M+H)+=410.

Workup

  1. custompurified in a manner similar to Example 117

Sources & evidence

ORD record
ord-b36d178eee754a7dbdfbb347ecf5e0ea
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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