Sodium Chloride → HCID 22504455, compound

HRID 1432287Notes

Reaction equation

HRID 1432287 reaction equation
C[O:2][C:3]([C:5]1[N:17]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[C:8]2=[N:9][CH:10]=[C:11]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:12]=[C:7]2[CH:6]=1)=O.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Na+].[Cl-]>C(OCC)(=O)C>[F:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][N:17]2[C:8]3=[N:9][CH:10]=[C:11]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:12]=[C:7]3[CH:6]=[C:5]2[CH2:3][OH:2])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 68444621HCID 68444621, compound

Product 1

HCID 22504455HCID 22504455, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1-(4-fluorobenzyl)-5-methanesulfonyl-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid methyl ester (0.49 g) and tetrahydrofuran (14 ml), lithium aluminum hydride (77 mg) was added at 0° C. and the mixture was stirred at the same temperature for 15 minutes. The mixture was diluted with ethyl acetate and a saturated aqueous NaCl solution was added thereto. The mixture was dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was separated using silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain the desired product (0.39 g) as a white powder.

Workup

  1. additionwas added at 0° C.
  2. dry with materialThe mixture was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was separated

Sources & evidence

ORD record
ord-2cf3356006d74f6d937fa09d22b6b21c
Source dataset
uspto-grants-2009_11
Patent number
US07612070B2

Reaction notes

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