Tetrahydrofuran → HCID 67169028, compound

HRID 1517600Notes

Reaction equation

HRID 1517600 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O[C:10]([C:12]1[C:13]([CH3:24])=[N:14][N:15]([C:17]2[C:22](Br)=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:16]=1)=[O:11])C.O1[CH2:29][CH2:28][CH2:27]C1>>[CH:27]1([C:22]2[C:17]([N:15]3[CH:16]=[C:12]([CH2:10][OH:11])[C:13]([CH3:24])=[N:14]3)=[N:18][CH:19]=[CH:20][CH:21]=2)[CH2:28][CH2:29]1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 67168187HCID 67168187, compound

Product 1

HCID 67169028HCID 67169028, compoundYield 84%

Procedure

To a stirred suspension of lithium aluminium hydride (0.44 g, 11.7 mmol) in dry tetrahydrofuran (25 mL) is added a solution of 1-(3-bromo-pyridin-2-yl)-3-methyl-pyrazole-4-carboxylic acid ethyl ester (1.6 g, 5.8 mmol) in dry tetrahydrofuran (5 mL) under nitrogen atmosphere at −78° C. After complete addition the reaction mixture is warmed to room temperature then stir overnight. The reaction mixture is quenched with 1N sodium hydroxide then filtered through the celite. The organic layer is separated and the aqueous layer is extracted with ethyl acetate. The combined organic layer is washed with water and brine, dried on sodium sulfate, filtered and concentrated to yield 1.1 g (84%) of [1-(3-cyclopropyl-pyridin-2-yl)-3-methyl-pyrazol-4-yl]-methanol. MS (m/z): 230 (M+1).

Workup

  1. additionAfter complete addition the reaction mixture
  2. customThe reaction mixture is quenched with 1N sodium hydroxide
  3. filtrationthen filtered through the celite
  4. customThe organic layer is separated
  5. extractionthe aqueous layer is extracted with ethyl acetate
  6. washThe combined organic layer is washed with water and brine
  7. customdried on sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d575b1fb9ad84f678bb94e12ca90efb4
Source dataset
uspto-grants-2012_07
Patent number
US08232289B2

Reaction notes

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