Cyclopropanecarbonyl chloride → HCID 60205356, compound

HRID 875701Notes

Reaction equation

HRID 875701 reaction equation
[Br:1][C:2]1[C:3]([F:12])=[C:4]2[C:10]([NH2:11])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH:13]1([C:16](Cl)=[O:17])[CH2:15][CH2:14]1.O.[OH-].[Li+]>N1C=CC=CC=1.C1COCC1.O>[Br:1][C:2]1[C:3]([F:12])=[C:4]2[C:10]([NH:11][C:16]([CH:13]3[CH2:15][CH2:14]3)=[O:17])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 168937Lithium hydroxide, monohydrateHCID 602052765-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

Product 1

HCID 60205356HCID 60205356, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (200 mg, 0.869 mmol) in pyridine (5 mL) at 0° C. was treated dropwise with cyclopropanecarbonyl chloride (118.3 μL, 1.304 mmol). The mixture was stirred at 0° C. for 60 minutes, and then the pyridine was removed in vacuo. The residue obtained was dissolved in THF (10 mL) and treated with lithium hydroxide hydrate (109.5 mg, 2.61 mmol) in water (1 mL). After 30 minutes, the THF was removed under reduced pressure, and water (5 mL) was added to the residue. The solid formed was filtered, washed with additional water and dried to provide N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)cyclopropanecarboxamide (165 mg, 64% yield) as a solid. 1H NMR (400 MHz, (CD3)2SO) δ 12.03 (br s, 1H), 9.76 (s, 1H), 8.34 (d, 1H), 7.59 (s, 1H), 1.93-1.86 (m, 1H), 0.783 (d, 4H); LCMS (APCI+) m/z 298, 300 (M+H)+, Retention time=2.71 min (Method 2).

Workup

  1. customthe pyridine was removed in vacuo
  2. customThe residue obtained
  3. waitAfter 30 minutes
  4. customthe THF was removed under reduced pressure, and water (5 mL)
  5. additionwas added to the residue
  6. customThe solid formed
  7. filtrationwas filtered
  8. washwashed with additional water
  9. customdried

Sources & evidence

ORD record
ord-e3309d28dba14d32a1e1d467b78a6096
Source dataset
uspto-grants-2015_03
Patent number
US08981085B2

Reaction notes

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