Triethylamine → HCID 60205688, compound

HRID 1923948Notes

Reaction equation

HRID 1923948 reaction equation
[CH3:1][S:2]([CH2:5][C:6]([OH:8])=O)(=[O:4])=[O:3].O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.C(N(CC)CC)C.[Br:31][C:32]1[C:33]([F:42])=[C:34]2[C:40]([NH2:41])=[CH:39][NH:38][C:35]2=[N:36][CH:37]=1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:31][C:32]1[C:33]([F:42])=[C:34]2[C:40]([NH:41][C:6](=[O:8])[CH2:5][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:39][NH:38][C:35]2=[N:36][CH:37]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 37328412-Methanesulfonylacetic acidHCID 602052765-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

Product 1

HCID 60205688HCID 60205688, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(Methylsulfonyl)acetic acid (601 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-(methylsulfonyl)acetamide (503 mg, 66.1% 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-eebe645458f44fb5834e3e3680ce56be
Source dataset
uspto-grants-2012_05
Patent number
US08178131B2

Reaction notes

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