Methanesulfonic Acid → HCID 67383001, compound

HRID 335872Notes

Reaction equation

HRID 335872 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[N:15]=[CH:14][C:13]([I:16])=[CH:12][C:8]=2[C:9]([OH:11])=O)=[CH:4][C:3]=1[F:19].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.CS(O)(=O)=O.BrC1C(F)=C2C(=CC=1)OC1=NC=C(I)C=C1C2=O>>[Br:1][C:2]1[CH:18]=[C:17]2[C:5](=[CH:4][C:3]=1[F:19])[O:6][C:7]1=[N:15][CH:14]=[C:13]([I:16])[CH:12]=[C:8]1[C:9]2=[O:11]

Participants

5

Reactant 4

HCID 6395Methanesulfonic AcidHCID 14812Phosphorus oxide (P4O10)HCID 67383179HCID 67383179, compoundHCID 67383369HCID 67383369, compound

Product 1

HCID 67383001HCID 67383001, compoundYield 78.3%

Procedure

A flask charged with 2-(4-bromo-3-fluorophenoxy)-5-iodonicotinic acid (109 g, 249 mmol) and phosphorus pentoxide (70.6 g, 497 mmol) was treated with methanesulfonic acid (484 mL, 7460 mmol). After stirring for 30 minutes at room temperature, the reaction mixture was heated to 120° C. for 18 h. The reaction mixture was allowed to cool to room temperature and was poured into 1 L of ice water. After stirring for one hour, the resulting solid was filtered and subsequently washed sequentially with water and MeOH. The solid was dried to provide a 1:4 mixture of 7-bromo-6-fluoro-3-iodo-5H-chromeno[2,3-b]pyridin-5-one and 7-bromo-8-fluoro-3-iodo-5H-chromeno[2,3-b]pyridin-5-one (81.92 g, 195 mmol, 78% yield) as an off white solid.

Workup

  1. temperaturethe reaction mixture was heated to 120° C. for 18 h
  2. temperatureto cool to room temperature
  3. stirringAfter stirring for one hour
  4. filtrationthe resulting solid was filtered
  5. washsubsequently washed sequentially with water and MeOH
  6. customThe solid was dried
  7. customto provide

Sources & evidence

ORD record
ord-722781f0c0b3438b9a6dd7af9c943236
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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