Phenylacetic Acid → N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-phenylacetamide

HRID 1034918

Reaction equation

HRID 1034918 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.C(N(CC)CC)C.[Br:33][C:34]1[C:35]([F:44])=[C:36]2[C:42]([NH2:43])=[CH:41][NH:40][C:37]2=[N:38][CH:39]=1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:33][C:34]1[C:35]([F:44])=[C:36]2[C:42]([NH:43][C:8](=[O:10])[CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:41][NH:40][C:37]2=[N:38][CH:39]=1

Participants

7

Reactant 5

HCID 999Phenylacetic AcidHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 602052765-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

Product 1

HCID 60205702N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-phenylacetamideYield 80.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Phenylacetic acid (592 mg, 4.35 mmol), bis(2-oxooxazolidin-3-yl)phosphinic chloride (1107 mg, 4.35 mmol) and triethylamine (1100 mg, 10.9 mmol) were added to 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (500 mg, 2.17 mmol) in DCM (100 mL). The reaction mixture was stirred at room temperature for 1 hour, and then 2N aqueous Na2CO3 (50 mL) was added. The resulting suspension was filtered, and the solid was rinsed with DCM and water. After drying, N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-phenylacetamide (606 mg, 80.1% yield) was obtained as a solid.

Workup

  1. filtrationThe resulting suspension was filtered
  2. washthe solid was rinsed with DCM and water
  3. customAfter drying

Sources & evidence

ORD record
ord-688ff7caaecb4cf1a0a6f8467dc7af82
Source dataset
uspto-grants-2013_10
Patent number
US08545897B2

Linked notes

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