Cesium carbonate → HCID 68360801, compound

HRID 1852399Notes

Reaction equation

HRID 1852399 reaction equation
F[C:2]1[C:3]([N+:18]([O-:20])=[O:19])=[C:4]([CH:14]=[C:15]([F:17])[CH:16]=1)[NH:5][C:6]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][C:7]=1[F:13].[OH:21][C:22]1[CH:23]=[C:24]([CH:38]=[CH:39][CH:40]=1)[CH2:25][NH:26][S:27]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])(=[O:29])=[O:28].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[F:17][C:15]1[CH:14]=[C:4]([NH:5][C:6]2[CH:11]=[CH:10][C:9]([I:12])=[CH:8][C:7]=2[F:13])[C:3]([N+:18]([O-:20])=[O:19])=[C:2]([CH:16]=1)[O:21][C:22]1[CH:23]=[C:24]([CH:38]=[CH:39][CH:40]=1)[CH2:25][NH:26][S:27]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 10796Cesium carbonate2×HCID 57625029HCID 57625029, compound2×HCID 68360917HCID 68360917, compound3×

Product 1

HCID 68360801HCID 68360801, compoundYield 140.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.0 g of 3,5-difluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline (Intermediate 1A; 64% pure, 3.25 mmol, 1 eq.), 0.98 g tert-butyl [(3-hydroxybenzyl)sulfamoyl]carbamate (Intermediate 2A; 3.24 mmol, 1 eq.) and 1.6 g caesium carbonate (4.9 mmol, 1.5 eq.) were suspended in 25 mL DMF and stirred in a closed vial at rt for 3 days. Additional 0.4 eq. tert-butyl [(3-hydroxybenzyl)sulfamoyl]carbamate and 0.4 eq. caesium carbonate were added and stirring was continued for 2 days. The reaction mixture was partitioned between sodium chloride solution and ether, the layers were separated and the aqueous layer was reextracted with ether. The combined organic layers were dried, filtered and concentrated in vacuo to yield 3.08 g of the crude product (as a regioisomeric mixture containing some unreacted starting material), which was used in the subsequent reaction without further purification.

Workup

  1. stirringstirring
  2. waitwas continued for 2 days
  3. customThe reaction mixture was partitioned between sodium chloride solution and ether
  4. customthe layers were separated
  5. customThe combined organic layers were dried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a6cdd856b7074efc9cbecae860e3ec69
Source dataset
uspto-grants-2015_02
Patent number
US08962606B2

Reaction notes

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