HCID 86716094, compound → HCID 86716095, compound

HRID 627532Notes

Reaction equation

HRID 627532 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:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[C:6]([CH:11]=1)[C:7]([O:9]C)=O.CO[Na]>O1CCCC1.CO>[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:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[C:7]2=[O:9]

Participants

5

Reactant 2

HCID 86716094HCID 86716094, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 86716095HCID 86716095, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

Into a 100-mL round-bottom flask was placed a solution of methyl 5-bromo-2-[2-(pyridin-3-yl)acetamido]benzoate (3 g, 7.73 mmol, 1.00 equivalent, purity 90%, Intermediate 51, step a) in tetrahydrofuran (30 mL). A 2.38 M solution of MeONa in MeOH (freshly prepared by dissolving 2.74 g of Na in 50 mL of anhydrous MeOH solution, 11.7 mL, 27.85 mmol, 4.00 equivalents) was then added. The resulting solution was stirred overnight at 20° C., and the precipitate was collected by filtration to give the title compound as a white solid.

Workup

  1. customInto a 100-mL round-bottom flask was placed
  2. additionwas then added
  3. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-28a23a78daaa4cdc8fbf372d0ddd3e70
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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