Dichloromethane → 4'-Methoxy-biphenyl-4-sulfonic acid (2-benzoyl-4-chloro-phenyl)-amide

HRID 2056306Notes

Reaction equation

HRID 2056306 reaction equation
[C:1]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[NH:16][S:17]([C:20]1[CH:25]=[CH:24][C:23](I)=[CH:22][CH:21]=1)(=[O:19])=[O:18])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCCl.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:36][O:37][C:38]1[CH:43]=[CH:42][C:41](B(O)O)=[CH:40][CH:39]=1>CN1C(=O)CCC1.C(N(CC)CC)C.COCCOC>[C:1]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[NH:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([C:41]2[CH:42]=[CH:43][C:38]([O:37][CH3:36])=[CH:39][CH:40]=2)=[CH:22][CH:21]=1)(=[O:19])=[O:18])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 10028837N-(2-benzoyl-4-chloro-phenyl)-4-iodo-benzenesulfonamide

Product 1

HCID 112945284'-Methoxy-biphenyl-4-sulfonic acid (2-benzoyl-4-chloro-phenyl)-amide

Reagents, catalysts & solvents 3

HCID 80711,2-DimethoxyethaneSolventHCID 8471TriethylamineSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
55 °C

Procedure

To a magnetically stirred mixture of N-(2-Benzoyl-4-chloro-phenyl)-4-iodo-benzenesulfonamide (497 mg, 1.0 mmol), [1,1′ Bis(diphenylphosphino)-ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (30 mg, 0.037 mmol) and dry cesium carbonate (511 mg, 1.57 mmol) in NMP (3 mL), was added DME (3 mL) and dry triethylamine (3 mL) under dry nitrogen. To this stirred mixture was added (4-methoxyphenyl)boronic acid (202 mg) and the mixture was stirred at 55° C. overnight. The reaction was worked up by addition to crushed ice and extracted with ethyl acetate (3×75 mL), and the organic layer was dried (MgSO4), filtered and concentrated. The crude product was chromatographed on silica gel using 10-30% EtOAc/Hexane. 1H NMR (CDCl3) δ 9.64 (br s, 1H, NH), 7.75 (dm, 1H), 7.75 (dm, 2H, J=8.8 Hz), 7.48 (m, 3H), 7.56 (dm, 2H, J=8.4 Hz), 7.51 (m), 7.32 (d 1H, J=2.2 Hz), 7.26 (d, 1H, J=7 Hz), 7.09 (d, 2H, J=8.4 Hz), 3.65 (s, 3H). MS: m/z 478.0 (M+1).

Workup

  1. additionThe reaction was worked up by addition
  2. customto crushed ice
  3. extractionextracted with ethyl acetate (3×75 mL)
  4. dry with materialthe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was chromatographed on silica gel using 10-30% EtOAc/Hexane

Sources & evidence

ORD record
ord-a81f91bb782a45c59b66a4d0169e74c4
Source dataset
uspto-grants-2008_02
Patent number
US07335653B2

Reaction notes

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