Lithium Hydroxide → HCID 60205501, compound

HRID 1034802Notes

Reaction equation

HRID 1034802 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.[O:13]1[CH2:17][CH2:16][CH2:15][C@H:14]1[C:18](O)=[O:19].C(N(CC)CC)C.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:18]([C@@H:14]3[CH2:15][CH2:16][CH2:17][O:13]3)=[O:19])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

8

Reactant 5

HCID 3939Lithium HydroxideHCID 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 446666Tetrahydro-2-furoic acid, (-)-HCID 602052765-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

Product 1

HCID 60205501HCID 60205501, compoundYield 70.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (200 mg, 0.869 mmol), (S)-tetrahydrofuran-2-carboxylic acid (252 mg, 2.17 mmol), triethylamine (606 μL, 4.35 mmol), and BOP—Cl (203 mg, 2.17 mmol) in CH2Cl2 (10 mL) was stirred at room temperature for 7 hours. 2M LiOH (5 mL) was added then to the mixture and stirred at room temperature for 30 minutes. Water (25 mL) was then added and stirred for an additional 30 minutes. The solid formed was filtered, washed with water (3×5 mL) and dried to provide (S)—N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)tetrahydrofuran-2-carboxamide (202 mg, 70.8% yield) as a solid. LCMS (APCI+) m/z 327.9, 329.9 (M+H)+; Retention time=2.80 minutes (Method 2).

Workup

  1. stirringto the mixture and stirred at room temperature for 30 minutes
  2. stirringstirred for an additional 30 minutes
  3. customThe solid formed
  4. filtrationwas filtered
  5. washwashed with water (3×5 mL)
  6. customdried

Sources & evidence

ORD record
ord-94da5aa159524104af29c8c293928b07
Source dataset
uspto-grants-2013_10
Patent number
US08545897B2

Reaction notes

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