Lithium Hydroxide → HCID 60205402, compound

HRID 1034737Notes

Reaction equation

HRID 1034737 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.[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:20](O)=[O:21])=[N:18][CH:19]=1.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.[Li+].[OH-]>C(Cl)Cl.O>[Br:1][C:2]1[C:3]([F:12])=[C:4]2[C:10]([NH:11][C:20](=[O:21])[C:17]3[CH:16]=[CH:15][C:14]([Cl:13])=[CH:19][N:18]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 27628725-Chloro-2-picolinic acidHCID 602052765-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

Product 1

HCID 60205402HCID 60205402, compoundYield 74.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

TEA (0.61 mL, 4.35 mmol) was added to 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (200 mg, 0.87 mmol, Example 1, Step H), 5-chloropicolinic acid (160 mg, 1.04 mmol) and BOP—Cl (332 mg, 1.30 mmol) in DCM (5 mL). The reaction was stirred at room temperature for 1 hour, and then a LiOH solution (2 N, 3 mL) was added. The mixture was stirred for 30 minutes, and water (10 mL) was added. The solid formed was collected by filtration, washed with DCM (10 mL) and dried to give N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-chloropicolinamide (240 mg, 73% yield) as a solid.

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. customThe solid formed
  3. filtrationwas collected by filtration
  4. washwashed with DCM (10 mL)
  5. customdried

Sources & evidence

ORD record
ord-e94d871663d9493da65f439719ec191a
Source dataset
uspto-grants-2013_10
Patent number
US08545897B2

Reaction notes

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