4-bromo-N-(1,3-thiazol-2-yl)benzene-1-sulfonamide → HCID 59466169, compound

HRID 1696132Notes

Reaction equation

HRID 1696132 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(O)(=O)C.[NH:21]1[CH2:24][CH:23]([CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:22]1.CC(C)([O-])C.[Na+].C1(C2C=CC=CC=2)C=CC=CC=1P(C(C)(C)C)C(C)(C)C>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[C:29]([O:28][C:27](=[O:33])[NH:26][CH2:25][CH:23]1[CH2:22][N:21]([C:2]2[CH:7]=[CH:6][C:5]([S:8](=[O:10])(=[O:9])[NH:11][C:12]3[S:13][CH:14]=[CH:15][N:16]=3)=[CH:4][CH:3]=2)[CH2:24]1)([CH3:32])([CH3:30])[CH3:31]

Participants

8

Reactant 4

HCID 6693044-bromo-N-(1,3-thiazol-2-yl)benzene-1-sulfonamideHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxideHCID 53627632HCID 53627632, compound

Product 1

HCID 59466169HCID 59466169, compoundYield 22%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Prepared using general procedure 24. A solution of 4-bromo-N-(thiazol-2-yl)benzenesulfonamide (2.0 g, 6.3 mmol), tert-butyl azetidin-3-ylmethylcarbamate acetate (1.71 g, 6.93 mmol), sodium tert-butoxide (2.55 g, 26.5 mmol), biphenyl-2-yldi-tert-butylphosphine (224 mg, 0.76 mmol), and Pd2(dba)3 (172 mg, 0.19 mmol) in toluene (16 mL) was stirred at 75° C. for 16 h. The reaction mixture was poured into H2O, and the pH was adjusted to 6. The aqueous layer was extracted 4 times with CH2Cl2, and the organics were combined, washed with saturated aqueous NaCl solution, dried over MgSO4, and concentrated. Purification via silica gel chromatography using 50-90% EtOAc in hexanes gave tert-butyl-(1-(4-(N-thiazol-2-ylsulfamoyl)phenyl)azetidin-3-yl)methylcarbamate (0.58 g, 22%). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=425.0; tR=2.59 min.

Workup

  1. customPrepared
  2. extractionThe aqueous layer was extracted 4 times with CH2Cl2
  3. washwashed with saturated aqueous NaCl solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customPurification via silica gel chromatography

Sources & evidence

ORD record
ord-6975186e7bec4676b14b8cbd22aab131
Source dataset
uspto-grants-2012_04
Patent number
US08163720B2

Reaction notes

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