HCID 86716104, compound → HCID 86716105, compound

HRID 1478486Notes

Reaction equation

HRID 1478486 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:13](=[O:21])[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[C:6]([CH:11]=1)[C:7]([O:9]C)=O.CO[Na]>O1CCCC1>[Br:1][C:2]1[CH:11]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:12][C:13](=[O:21])[CH:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[C:7]2=[O:9]

Participants

4

Reactant 2

HCID 86716104HCID 86716104, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 86716105HCID 86716105, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

Into a 250-mL round-bottom flask was placed a solution of methyl 5-bromo-2-[2-(pyridin-2-yl)acetamido]benzoate (3 g, 7.73 mmol, Intermediate 9: step a) and MeONa (11.7 mL, 31 mmol, 2.64 M in MeOH) in tetrahydrofuran (30 mL). The resulting solution was stirred overnight at 20° C. Then, the solvents were removed by a rotary evaporator and 50 mL water was added to the residue. The pH of the resulting mixture was adjusted to 7 with 1 M aqueous HCl. The solid was collected by filtration and dried under vacuum to afford the title compound as a white solid which was used in the next step without further purification.

Workup

  1. customInto a 250-mL round-bottom flask was placed
  2. customThen, the solvents were removed by a rotary evaporator and 50 mL water
  3. additionwas added to the residue
  4. filtrationThe solid was collected by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-fe150fc3884f4a439c0fd7362fbd2c4b
Source dataset
uspto-grants-2016_08
Patent number
US09403816B2

Reaction notes

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