Lithium Hydroxide → HCID 60205335, compound

HRID 408196Notes

Reaction equation

HRID 408196 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.[CH3:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][N:15]=1.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.C(N(CC)CC)C.[Li+].[OH-]>C(Cl)Cl.O>[Br:1][C:2]1[C:3]([F:12])=[C:4]2[C:10]([NH:11][C:18](=[O:19])[C:17]3[CH:21]=[CH:22][C:14]([CH3:13])=[N:15][CH:16]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

8

Reactant 5

HCID 3939Lithium HydroxideHCID 8471TriethylamineHCID 1378606-Methylnicotinic acidHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 602052765-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

Product 1

HCID 60205335HCID 60205335, compoundYield 68,316.398%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (250 mg, 1.09 mmol), 6-methylnicotinic acid (313 mg, 2.28 mmol), BOP-Cl (581 mg, 2.28 mmol), and triethylamine (0.757 mL, 5.43 mmol) in DCM (5 mL) was stirred at room temperature for 30 minutes. 3M LiOH (3 mL) was then added. The reaction was stirred for an additional 10 minutes and then poured into water. The mixture was then filtered, washed with DCM, washed with 10:1 DCM:MeOH and dried to give N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-6-methylnicotinamide (260 g, 68.5% yield) as a solid

Workup

  1. stirringThe reaction was stirred for an additional 10 minutes
  2. filtrationThe mixture was then filtered
  3. washwashed with DCM
  4. washwashed with 10:1 DCM
  5. dry with materialMeOH and dried

Sources & evidence

ORD record
ord-70ad39a14c8546a791c10683f8a26c36
Source dataset
uspto-grants-2014_06
Patent number
US08758830B2

Reaction notes

Loading…