Sodium Carbonate → HCID 74763520, compound

HRID 623366Notes

Reaction equation

HRID 623366 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:20])[F:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:26][S:27]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)(=[O:29])=[O:28].C([O-])([O-])=O.[Na+].[Na+]>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O1CCOCC1>[CH2:22]([N:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([F:21])([F:20])[F:19])[S:8]([C:5]1[CH:6]=[CH:7][C:2]([C:33]2[CH:34]=[CH:35][C:30]([S:27]([CH3:26])(=[O:29])=[O:28])=[CH:31][CH:32]=2)=[CH:3][CH:4]=1)(=[O:10])=[O:9])[CH:23]([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 86722206HCID 86722206, compound

Product 1

HCID 74763520HCID 74763520, compoundYield 78%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
150 °C

Procedure

A 2-5 mL microwave vial was charged with 4-bromo-N-isobutyl-N-(2-trifluoromethyl-phenyl)-benzenesulfonamide (108 mg, 0.248 mmol), 4-(methanesulfonyl)benzene boronic acid (60 mg, 0.298 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride (18 mg, 0.025 mmol), 1M Na2CO3 solution (496 μL, 0.496 mmol) and 1,4-dioxane (2.5 mL). The mixture was degassed, purged with nitrogen and heated at 150° C. for 30 minutes using microwave irradiation. The mixture was diluted with EtOAc, washed with water (2×) and brine dried over Na2SO4 and concentrated under vacuum. Purified by silica gel column chromatography (0-100% EtOAc in cyclohexane) and triturating with diethyl ether gave the title compound (99 mg, 78% yield) as a white solid. 1H NMR (400 MHz, DMSO) δ 8.06-8.03 (m, 6H), 7.85 (dd, J=7.4, 2.1 Hz, 1H), 7.80-7.74 (m, 2H), 7.69-7.60 (m, 2H), 7.07 (d, J=7.7 Hz, 1H), 3.47 (dd, J=13.4, 8.7 Hz, 1H), 3.29 (s, 3H), 3.21 (dd, J=13.4, 4.8 Hz, 1H), 1.56-1.45 (m, 1H), 0.91 (d, J=6.5 Hz, 3H), 0.74 (d, J=6.7 Hz, 3H), LCMS (m/z Method B) ES+ 512.0 [M+1]+.

Workup

  1. customThe mixture was degassed
  2. custompurged with nitrogen
  3. custommicrowave irradiation
  4. additionThe mixture was diluted with EtOAc
  5. washwashed with water (2×) and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under vacuum
  8. customPurified by silica gel column chromatography (0-100% EtOAc in cyclohexane)
  9. customtriturating with diethyl ether

Sources & evidence

ORD record
ord-d6c93de0cc054a1da9340b36c8c691e7
Source dataset
uspto-grants-2016_04
Patent number
US09302985B2

Reaction notes

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