Carbon Dioxide → HCID 90418240, compound

HRID 923697Notes

Reaction equation

HRID 923697 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[C:14]3[S:15][CH:16]=[CH:17][C:13]=3[CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([C:18]([O:20][CH3:21])=[O:19])[C:3]=1[Cl:22].C(=O)=O.[Br:26]Br>ClCCl>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[C:14]3[S:15][CH:16]=[C:17]([Br:26])[C:13]=3[CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([C:18]([O:20][CH3:21])=[O:19])[C:3]=1[Cl:22]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 24408BromineHCID 90418074HCID 90418074, compound

Product 1

HCID 90418240HCID 90418240, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-5 °C

Procedure

Methyl 4-amino-6-(benzo[b]thiophen-7-yl)-3-chloro-5-fluoropicolinate (0.500 g, 1.485 mmol) was dissolved in dichloromethane (9.90 mL) and cooled to −5° C. in a acetone bath to which was added a few pieces of dry ice. Bromine (114 mL, 2.227 mmol) was dissolved in dichloromethane (9.90 mL) and added dropwise. The reaction mixture was stirred overnight, and then partitioned between ethyl acetate and water. The organic phase was dried and concentrated and the product purified by flash chromatography (SiO2, 5-40% ethyl acetate/hexane gradient) followed by a second purification by reverse phase chromatography to provide the title compound as a grey solid (0.278 g, 45).

Workup

  1. additionadded dropwise
  2. custompartitioned between ethyl acetate and water
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. customthe product purified by flash chromatography (SiO2, 5-40% ethyl acetate/hexane gradient)
  6. customfollowed by a second purification by reverse phase chromatography

Sources & evidence

ORD record
ord-34a40e18acc94f319258bae08cc6cba5
Source dataset
uspto-grants-2016_03
Patent number
US09278985B2

Reaction notes

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