Cesium carbonate → HCID 68360870, compound

HRID 1852393Notes

Reaction equation

HRID 1852393 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].[C:21]([NH:28][C:29]1[CH:30]=[C:31]([OH:35])[CH:32]=[CH:33][CH:34]=1)([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:24]([O:23][C:21](=[O:22])[NH:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][C:2]2[CH:16]=[C:15]([F:17])[CH:14]=[C:4]([NH:5][C:6]3[CH:11]=[CH:10][C:9]([I:12])=[CH:8][C:7]=3[F:13])[C:3]=2[N+:18]([O-:20])=[O:19])[CH:30]=1)([CH3:27])([CH3:25])[CH3:26]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 312485tert-butyl N-(3-hydroxyphenyl)carbamateHCID 57625029HCID 57625029, compound2×

Product 1

HCID 68360870HCID 68360870, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.0 g of 3,5-difluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline (Intermediate 1A; 70% pure, 5.3 mmol, 1 eq.), 1.1 g N-Boc-3-amino-phenol (5.3 mmol, 1 eq.) and 3.4 g caesium carbonate (10.7 mmol, 1.5 eq.) were suspended in 30 mL DMF and stirred at rt for 16 h. LCMS analysis showed complete turnover. The reaction mixture was partitioned between water and ethyl acetate, the layers were separated and the aqueous layer was reextracted with ethyl acetate. The combined organic layers were dried, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography (n-hexane/ethyl acetate gradient) providing 1.35 of the desired product (44% yield).

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. customthe layers were separated
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash column chromatography (n-hexane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-c6e0a99acaae42deb6fb3cc03ec011f2
Source dataset
uspto-grants-2015_02
Patent number
US08962606B2

Reaction notes

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