ethyl 1-(oxan-2-yl)-4-{1H-pyrrolo[2,3-b]pyridin-4-yl}-1H-pyrazole-3-carboxylate → [1-(oxan-2-yl)-4-{1H-pyrrolo[2,3-b]pyridin-4-yl}-1H-pyrazol-3-yl]methanol

HRID 60180Notes

Reaction equation

HRID 60180 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]3[NH:18][CH:19]=[CH:20][C:13]=23)[C:9]([C:21](OCC)=[O:22])=[N:8]1>C1COCC1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]3[NH:18][CH:19]=[CH:20][C:13]=23)[C:9]([CH2:21][OH:22])=[N:8]1

Participants

3

Reactant 1

HCID 118025456ethyl 1-(oxan-2-yl)-4-{1H-pyrrolo[2,3-b]pyridin-4-yl}-1H-pyrazole-3-carboxylate

Product 1

HCID 118025563[1-(oxan-2-yl)-4-{1H-pyrrolo[2,3-b]pyridin-4-yl}-1H-pyrazol-3-yl]methanolYield 80.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 1-(oxan-2-yl)-4-{1H-pyrrolo[2,3-b]pyridin-4-yl}-1H-pyrazole-3-carboxylate (7.8 g, 22.94 mmol) in THF (100 mL), was added LiALH4 (3 g, 70 mmol) in three portions at 0° C. The resulting mixture was stirred at room temperature for overnight. When the reaction was deemed complete, it was quenched by water (3 mL), extracted with ethyl acetate. The combined organic layer was dried ove Na2SO4, filtered and concentrated in vacuo to give 5.5 g of the title compound as an off-white solid. [M+H] found 299.

Workup

  1. customit was quenched by water (3 mL)
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layer was dried ove Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1bdfa9ae9ce5472ea152aed2f2cae46c
Source dataset
uspto-grants-2016_09
Patent number
US09440977B2

Reaction notes

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