N-(3-bromo-4-(2,4-difluorophenoxy)phenyl)ethanesulfonamide → US10023592, Example 122

HRID 575610Notes

Reaction equation

HRID 575610 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:17][S:18]([CH2:21][CH3:22])(=[O:20])=[O:19])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[F:16].[F:23][C:24]1[C:25](=[O:40])[N:26]([CH3:39])[CH:27]=[C:28](B2OC(C)(C)C(C)(C)O2)[CH:29]=1>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:16][C:10]1[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:9]=1[O:8][C:7]1[CH:6]=[CH:5][C:4]([NH:17][S:18]([CH2:21][CH3:22])(=[O:20])=[O:19])=[CH:3][C:2]=1[C:28]1[CH:29]=[C:24]([F:23])[C:25](=[O:40])[N:26]([CH3:39])[CH:27]=1

Participants

6

Reactant 2

HCID 117770988N-(3-bromo-4-(2,4-difluorophenoxy)phenyl)ethanesulfonamideHCID 1238237903-Fluoro-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one

Product 1

HCID 90019338US10023592, Example 122Yield 35.4%

Reagents, catalysts & solvents 3

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

Procedure

N-[3-Bromo-4-(2,4-difluorophenoxy)phenyl]ethanesulfonamide (77 mg, 0.2 mmol), the title compound of Example 119, step 2 (50 mg, 0.2 mmol), and Pd(dppf)Cl2 (14 mg, 10%) in 1,4-dioxane (1 mL) and saturated bicarbonate solution (aq) (333 μL) were reacted, worked up and purified in a manner similar to Example 117. The title compound (31 mg, 27%) was obtained as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ 1.22 (t, J=7.3, 3 H) 3.11 (q, J=7.3 Hz, 2H) 3.55 (s, 3H) 6.86 (d, J=8.6 Hz, 1H) 7.02-7.12 (m, 1H) 7.13-7.23 (m, 2H) 7.26 (d, J=2.8 Hz, 1H) 7.35-7.52 (m, 1H) 7.60 (m, 1H) 7.79 (s, 1H) 9.48-9.96 (m, 1H). LCMS (M+H)+=439.

Workup

  1. custompurified in a manner similar to Example 117

Sources & evidence

ORD record
ord-4874a1d065cc45d3abf2e3ed9d33ab72
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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