3-Nitrophenylboronic Acid → HCID 58107458, compound

HRID 873693Notes

Reaction equation

HRID 873693 reaction equation
Br[C:2]1[CH:20]=[CH:19][C:5]([C:6]([C:8]2[CH:9]=[CH:10][C:11]([Cl:18])=[C:12]([S:14]([NH2:17])(=[O:16])=[O:15])[CH:13]=2)=[O:7])=[CH:4][CH:3]=1.[N+:21]([C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1)([O-:23])=[O:22]>O1CCOCC1.O.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>[Cl:18][C:11]1[CH:10]=[CH:9][C:8]([C:6]([C:5]2[CH:19]=[CH:20][C:2]([C:28]3[CH:27]=[CH:26][CH:25]=[C:24]([N+:21]([O-:23])=[O:22])[CH:29]=3)=[CH:3][CH:4]=2)=[O:7])=[CH:13][C:12]=1[S:14]([NH2:17])(=[O:16])=[O:15]

Participants

5

Reactant 2

HCID 16773-Nitrophenylboronic AcidHCID 44235745HCID 44235745, compound

Product 1

HCID 58107458HCID 58107458, compoundYield 20.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A mixture of 220 mg of 5-(4-bromo-benzoyl)-2-chloro-benzenesulfonamide (0.587 mmol, 1 equivalent), 196 mg of 3-nitrobenzene boronic acid (1.174 mmol, 2 equivalent), 556 mg of Ba(OH)2 (1.761 mmol, 3 equivalent), and 14 mg of Pd(PPh3)4 in degassed dioxane/water (30 mL/10 mL) is refluxed for 18 h. The reaction is quenched with 1 N HCl and extracted with ethyl acetate. The combined organic extracts are dried over sodium sulfate, and concentrated in vacuo. After purification by flash chromatography, 50 mg of the title compound is obtained as white solid. 1H NMR (400 MHz, CDCl3): δ 5.2 (br, 2H), 6.18 (br, 1H), 7.02 (d, 2H, J=8 Hz), 7.12-7.45 (m, 5H), 7.6-7.8 (m, 3H), 7.90 (dd, 1H), 8.41 (s, 1H). MS (m/z): 387 (M+1).

Workup

  1. temperatureis refluxed for 18 h
  2. customThe reaction is quenched with 1 N HCl
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic extracts are dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customAfter purification by flash chromatography

Sources & evidence

ORD record
ord-d666279622f045d692a85cf203fbfbc2
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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