Water → 3'-amino-N-methylbiphenyl-4-sulfonamide

HRID 1665735Notes

Reaction equation

HRID 1665735 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:13][C:14]1[CH:19]=[C:18]([C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=2)[CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 922693-Aminophenylboronic acidHCID 1012154-bromo-N-methylbenzene-1-sulfonamide

Product 1

HCID 592061913'-amino-N-methylbiphenyl-4-sulfonamideYield 50%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-bromo-N-methyl-benzene sulfonamide (2.49 g, 10 mmol) in DMF (20 mL) was added 3-amino-phenyl boronic acid (1.51 g, 11 mmol), Pd(PPh3)4 (90 mg, 0.30 mmol), potassium carbonate (1.52 g, 11 mmol) and water (5 mL). The resulting mixture was degassed by gently bubbling argon through the solution for 5 minutes at 20° C. The reaction mixture was then heated at 80° C. overnight. The reaction was filtered through a pad of silica gel, which was washed with CH2Cl2 (50 mL×3). The combined organics were concentrated under reduced pressure to give crude product, which was washed with EtOAc to give pure 3′-amino-N-methylbiphenyl-4-sulfonamide (C-3) (1.3 g, 50%). 1H NMR (300 MHz, CDCl3) δ 7.85 (d, J=8.7 Hz, 2 H), 7.75 (d, J=8.7 Hz, 2 H), 7.19 (t, J=7.8 Hz, 1 H), 6.95-7.01 (m, 2 H), 6.73-6.77 (m, 1 H), 2.54 (s, 3 H). MS (ESI) m/e (M+H+) 263.0.

Workup

  1. customThe resulting mixture was degassed by gently bubbling argon through the solution for 5 minutes at 20° C
  2. filtrationThe reaction was filtered through a pad of silica gel, which
  3. washwas washed with CH2Cl2 (50 mL×3)
  4. concentrationThe combined organics were concentrated under reduced pressure
  5. customto give crude product, which
  6. washwas washed with EtOAc

Sources & evidence

ORD record
ord-b4b7384e02c04ca7a400ea0820941725
Source dataset
uspto-grants-2011_10
Patent number
US08039491B2

Reaction notes

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