Sodium Hydroxide → HCID 69228934, compound

HRID 2250423Notes

Reaction equation

HRID 2250423 reaction equation
C[O:2][C:3]([C:5]1[NH:13][C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[CH:6]=1)=[O:4].[H-].[Na+].Br[CH2:17][C:18]1[CH:22]=[C:21]([C:23]2[S:24][C:25]([Cl:28])=[CH:26][CH:27]=2)[O:20][N:19]=1.[OH-].[Na+]>CN(C=O)C>[Cl:28][C:25]1[S:24][C:23]([C:21]2[O:20][N:19]=[C:18]([CH2:17][N:13]3[C:8]4=[N:9][CH:10]=[CH:11][CH:12]=[C:7]4[CH:6]=[C:5]3[C:3]([OH:2])=[O:4])[CH:22]=2)=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 111501463-Bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazoleHCID 17390026methyl 1H-pyrrolo(2,3-b)pyridine-2-carboxylate

Product 1

HCID 69228934HCID 69228934, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.195 g (1.1 mmol) of 1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid methyl ester was dissolved in 4 mL of DMF and 48.7 mg (1.2 mmol) of sodium hydride (60% in mineral oil) was added. The reaction was stirred at RT for 20 min, cooled to −78° C. then 324 mg (1.2 mmol) of 3-bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazole [prepared by adopting a procedure described by Ewing, William R.; Becker, Michael R.; Choi-Sledeski, Yong Mi; Pauls, Heinz W.; He, Wei; Condon, Stephen M.; Davis, Roderick S.; Hanney, Barbara A.; Spada, Alfred P.; Burns, Christopher J.; Jiang, John Z.; Li, Aiwen; Myers, Michael R; Lau, Wan F.; Poli, Gregory B; PCT Int. Appl. (2001) 460 pp. WO 0107436 A2] was added. The reaction was allowed to warm to RT overnight. 0.3 mL of 2N aqueous sodium hydroxide was added and the reaction was stirred at RT for 24 h. The product was purified by preparative RP-HPLC eluting with a gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid). After lyophilization the product was obtained as a solid.

Workup

  1. temperaturecooled to −78° C.
  2. temperatureto warm to RT overnight
  3. stirringthe reaction was stirred at RT for 24 h
  4. customThe product was purified by preparative RP-HPLC
  5. washeluting with a gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid)
  6. customAfter lyophilization the product was obtained as a solid

Sources & evidence

ORD record
ord-e6d389003177481e9ee6029516b536db
Source dataset
uspto-grants-2008_01
Patent number
US07317027B2

Reaction notes

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