Cyclopropanecarbonyl chloride → HCID 60205356, compound

HRID 408214Notes

Reaction equation

HRID 408214 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-4bb35827cebb45d0a9b00378ee4b3955
Source dataset
uspto-grants-2014_06
Patent number
US08758830B2

Reaction notes

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