Lithium Hydroxide → HCID 60205339, compound

HRID 408199

Reaction equation

HRID 408199 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=O.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.[Li+].[OH-].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:7](=[O:9])[C:6]3[CH:10]=[C:2]([CH3:1])[CH:3]=[N:4][CH:5]=3)=[CH:41][NH:40][C:37]2=[N:38][CH:39]=1

Participants

8

Reactant 6

HCID 3939Lithium HydroxideHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 2562085-Methylnicotinic acidHCID 602052765-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

Product 1

HCID 60205339HCID 60205339, compoundYield 37.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Methylnicotinic acid (477 mg, 3.48 mmol), bis(2-oxooxazolidin-3-yl)phosphinic chloride (885 mg, 3.48 mmol) and triethylamine (880 mg, 8.69 mmol) were added to 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (400 mg, 1.74 mmol) in DCM (200 mL). The reaction was stirred at room temperature for 1 hour, and then 3M aqueous LiOH (4 mL) was added. The reaction was stirred for 1 hour, and then saturated aqueous Na2CO3 was added (200 mL). The aqueous phase was extracted once with DCM (200 mL), and then the aqueous phase was filtered. The filtered cake was dried to yield N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-methylnicotinamide (228 mg, 37.6% yield) as a solid.

Workup

  1. stirringThe reaction was stirred for 1 hour
  2. extractionThe aqueous phase was extracted once with DCM (200 mL)
  3. filtrationthe aqueous phase was filtered
  4. customThe filtered cake was dried

Sources & evidence

ORD record
ord-b9e224e1b3fc4288b4293b91d241e14c
Source dataset
uspto-grants-2014_06
Patent number
US08758830B2

Linked notes

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