Dichloromethane → N-tert-Butyl-3'-fluoro-4'-quinoxalin-6-ylbiphenyl-2-sulfonamide

HRID 1523943Notes

Reaction equation

HRID 1523943 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([S:14]([NH:17][C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:16])=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][C:3]=1[F:22].CC1(C)C(C)(C)OB([C:31]2[CH:32]=[C:33]3[C:38](=[CH:39][CH:40]=2)[N:37]=[CH:36][CH:35]=[N:34]3)O1.C([O-])([O-])=O.[Na+].[Na+].C(Cl)Cl>C(OCC)(=O)C.O.O1CCOCC1>[C:18]([NH:17][S:14]([C:9]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:31]3[CH:32]=[C:33]4[C:38](=[CH:39][CH:40]=3)[N:37]=[CH:36][CH:35]=[N:34]4)=[C:3]([F:22])[CH:4]=2)=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:16])=[O:15])([CH3:21])([CH3:20])[CH3:19]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 441182986-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxalineHCID 903130764'-Bromo-N-(tert-butyl)-3'-fluoro-[1,1'-biphenyl]-2-sulfonamide

Product 1

HCID 90313194N-tert-Butyl-3'-fluoro-4'-quinoxalin-6-ylbiphenyl-2-sulfonamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

4′-Bromo-N-(tert-butyl)-3′-fluoro-[1,1′-biphenyl]-2-sulfonamide (30 mg, 0.078 mmol) and 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline (12 mg, 0.085 mmol) were added to a 5 mL sealable vial equipped with a stir bar. Dioxane (0.2 mL) and 2 M Na2CO3 (0.2 mL) were added. Argon was bubbled through the solvent while it was rapidly stirred for 10 min then Pd(dppf)Cl2.CH2Cl2 (3 mg, 0.004 mmol) was added, and the mixture heated for 15 hours at 80° Celsius under an argon atmosphere. The reaction was diluted with 2 mL of ethyl acetate and 2 mL of water and the aqueous layer was extracted with ethyl acetate (3×10 mL). The combined organic extracts were then dried with Na2SO4 and concentrated to dryness. The crude product was purified by HPLC to give the title compound. MS (ESI): mass calcd. for C24H22FN3O2S, 435.14; m/z found, 436.4 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 8.93-8.91 (d, J=1.8, 1H), 8.91-8.89 (d, J=1.8, 1H), 8.37-8.34 (m, 1H), 8.24-8.22 (m, 1H), 8.22-8.20 (m, 1H), 8.09-8.04 (m, 1H), 7.71-7.66 (m, 1H), 7.65-7.59 (m, 1H), 7.58-7.52 (m, 1H), 7.51-7.44 (dd, J=7.9, 1.8, 1H), 7.44-7.40 (dd, J=11.3, 1.7, 1H), 7.40-7.36 (dd, J=7.5, 1.4, 1H), 3.74 (s, 1H), 1.10 (s, 9H).

Workup

  1. customequipped with a stir bar
  2. customArgon was bubbled through the solvent while it
  3. extractionthe aqueous layer was extracted with ethyl acetate (3×10 mL)
  4. dry with materialThe combined organic extracts were then dried with Na2SO4
  5. concentrationconcentrated to dryness
  6. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-52382f87834f48cfa03c3c0218e60069
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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