Triethylamine → HCID 60205698, compound

HRID 408433Notes

Reaction equation

HRID 408433 reaction equation
[C:1]1([CH:7]([CH3:11])[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:34][C:35]1[C:36]([F:45])=[C:37]2[C:43]([NH2:44])=[CH:42][NH:41][C:38]2=[N:39][CH:40]=1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:34][C:35]1[C:36]([F:45])=[C:37]2[C:43]([NH:44][C:8](=[O:10])[CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH3:11])=[CH:42][NH:41][C:38]2=[N:39][CH:40]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 102962-Phenylpropionic acidHCID 10340Sodium CarbonateHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 602052765-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

Product 1

HCID 60205698HCID 60205698, compoundYield 48.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Phenylpropanoic acid (653 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 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-phenylpropanamide (384 mg, 48.8% 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-5d79e38198504f52b358e4b4b248b205
Source dataset
uspto-grants-2014_06
Patent number
US08758830B2

Reaction notes

Loading…