Lithium Hydroxide → HCID 60205498, compound

HRID 2203880Notes

Reaction equation

HRID 2203880 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](Cl)=[O:9].[Br:11][C:12]1[C:13]([F:22])=[C:14]2[C:20]([NH2:21])=[CH:19][NH:18][C:15]2=[N:16][CH:17]=1.[Li+].[OH-]>N1C=CC=CC=1.C1COCC1>[Br:11][C:12]1[C:13]([F:22])=[C:14]2[C:20]([NH:21][C:8](=[O:9])[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=3)=[CH:19][NH:18][C:15]2=[N:16][CH:17]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 135033Picolinoyl Chloride HydrochlorideHCID 602052765-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

Product 1

HCID 60205498HCID 60205498, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

Picolinoyl chloride hydrochloride (501 mg, 2.82 mmol) was added to a solution of 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (324 mg, 1.41 mmol, Example 1, Step H) in pyridine (5 mL). The reaction was stirred at room temperature for 10 minutes, and the pyridine was removed in vacuo. The residue obtained was dissolved in THF (5 mL), treated with 2N LiOH (3 mL), and stirred for 20 minutes. THF was then removed in vacuo, and water (20 mL) was added. The solid formed was collected by filtration and dried to provide N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)picolinamide (389 mg, 82% yield) as a solid. 1H NMR (400 MHz, (CD3)2SO) δ 12.17 (br s, 1H), 10.39 (s, 1H), 8.76 (d, 1H), 8.40 (d, 1H), 8.17-8.15 (m, 1H), 8.09 (dt, 1H), 7.87 (d, 1H), 7.71-7.68 (m, 1H).

Workup

  1. customthe pyridine was removed in vacuo
  2. customThe residue obtained
  3. stirringstirred for 20 minutes
  4. customTHF was then removed in vacuo, and water (20 mL)
  5. additionwas added
  6. customThe solid formed
  7. filtrationwas collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-4411c7d13a5a48d5ac702c25b98d5402
Source dataset
uspto-grants-2016_06
Patent number
US09365568B2

Reaction notes

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