Water → HCID 60205455, compound

HRID 875771Notes

Reaction equation

HRID 875771 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.[CH2:13]([CH:15]([CH2:19][CH3:20])[C:16](Cl)=[O:17])[CH3:14].[Li+].[OH-].O>N1C=CC=CC=1>[Br:1][C:2]1[C:3]([F:12])=[C:4]2[C:10]([NH:11][C:16](=[O:17])[CH:15]([CH2:19][CH3:20])[CH2:13][CH3:14])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 759542-Ethylbutyryl chlorideHCID 602052765-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

Product 1

HCID 60205455HCID 60205455, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (200 mg, 0.869 mmol, Example 1, Step H) in pyridine at 0° C. was treated dropwise with 2-ethylbutanoyl chloride (176 mg, 1.30 mmol). After 7 hours, 2M LiOH (5 mL) was added to the mixture and stirring was continued at room temperature for 30 minutes. Water (25 mL) was then added, and the solid formed was filtered, washed with water (3×5 mL) and dried to provide N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-ethylbutanamide (235 mg, 82% yield) as a solid. 1H NMR (400 MHz, (CD3)2SO) δ 12.06 (s, 1H), 9.46 (s, 1H), 8.34 (d, 1H), 7.53 (s, 1H), 2.30-2.24 (m, 1H), 1.62-1.52 (m, 2H), 1.47-1.41 (m, 2H), 0.90 (t, 6H); LCMS (APCI+) m/z 328, 330 (M+H)+, Retention time=3.20 minutes (Method 2).

Workup

  1. waitwas continued at room temperature for 30 minutes
  2. customthe solid formed
  3. filtrationwas filtered
  4. washwashed with water (3×5 mL)
  5. customdried

Sources & evidence

ORD record
ord-ed3edf75d1a04529b79ef9df8a23ef2f
Source dataset
uspto-grants-2015_03
Patent number
US08981085B2

Reaction notes

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