Ethanesulfonyl chloride → HCID 67074264, compound

HRID 1852389Notes

Reaction equation

HRID 1852389 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[O:5][C:6]1[C:7]([N+:22]([O-:24])=[O:23])=[C:8]([CH:18]=[C:19]([F:21])[CH:20]=1)[NH:9][C:10]1[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:11]=1[F:17].NC1C=C(C=CC=1)OC1C=C(F)C([N+]([O-])=O)=C(C=1)NC1C=CC(I)=CC=1F.[CH2:55]([S:57](Cl)(=[O:59])=[O:58])[CH3:56].FC1C([N+]([O-])=O)=C(C=C(NC2C=CC(I)=CC=2F)C=1)OC1C=C(NS(CC)(=O)=O)C=CC=1>N1C=CC=CC=1>[F:21][C:19]1[CH:18]=[C:8]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:11]=2[F:17])[C:7]([N+:22]([O-:24])=[O:23])=[C:6]([CH:20]=1)[O:5][C:4]1[CH:3]=[C:2]([NH:1][S:57]([CH2:55][CH3:56])(=[O:59])=[O:58])[CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 11667Ethanesulfonyl chlorideHCID 67073958HCID 67073958, compoundHCID 67074124HCID 67074124, compoundHCID 67074399HCID 67074399, compound

Product 1

HCID 67074264HCID 67074264, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

11.7 g 3-(3-aminophenoxy)-5-fluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline (24.3 mmol, 1. eq.; containing a minor amount of the regioisomeric 5-(3-aminophenoxy)-3-fluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline) was dissolved in 98 mL pyridine, set under an atmosphere of nitrogen and treated sequentially with 3.4 mL ethyl sulfonyl chloride (36.4 mmol, 1.5 eq.; dissolved in pyridine). The resulting reaction mixture was stirred at rt for 20 h after which LCMC analysis showed final turnover. The reaction mixture was quenched by addition of water and diluted with ethyl acetate and phases were separated. The separated aqueous layer was reextracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to give 14.8 g of the crude target compound (which contained a minor amount of the regioisomeric N-(3-{3-fluoro-5-[(2-fluoro-4-iodophenyl)amino]-2-nitrophenoxy}-phenyl)ethanesulfonamide) which was used without further purification in the subsequent transformations.

Workup

  1. customThe resulting reaction mixture
  2. customThe reaction mixture was quenched by addition of water
  3. additiondiluted with ethyl acetate and phases
  4. customwere separated
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give 14.8 g of the crude target compound (which
  10. customwas used without further purification in the subsequent transformations

Sources & evidence

ORD record
ord-317c74564e144d51a51b396ef0e90529
Source dataset
uspto-grants-2015_02
Patent number
US08962606B2

Reaction notes

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