Ethyl Acetate → (5-chloro-1-(4-fluorobutyl)-1H-pyrrolo[2,3-c]pyridin-2-yl)methanol

HRID 523470Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([C:11](OCC)=[O:12])[N:8]([CH2:16][CH2:17][CH2:18][CH2:19][F:20])[C:5]2=[CH:6][N:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OC(=O)C)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([CH2:11][OH:12])[N:8]([CH2:16][CH2:17][CH2:18][CH2:19][F:20])[C:5]2=[CH:6][N:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of ethyl 5-chloro-1-(4-fluorobutyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxylate 10-c (2.19 g, 7.3 mmoles) in THF (150 mL) was added lithium aluminium hydride (8.064 mL, 1.1 eq, 1M in THF) at −75° C. under a nitrogen atmosphere. The reaction was allowed to stir on the cooling bath for two hours while it was slowly warming up until 0° C. Then the mixture was cooled on an ice ethanol bath and carefully decomposed by adding 150 mL ethylacetate followed by 10 g of Na2SO4.10H2O. The mixture was stirred for one hour and then dried over MgSO4, filtered off and the filtrate was evaporated. The residue was purified over silica with dichloromethane/methanol 95/5 as eluent to give 550 mg (30% yield) of the targeted compound 10. m/z=257 (M+H)+.

Workup

temperatureThen the mixture was cooled on an ice ethanol bath
stirringThe mixture was stirred for one hour
dry with materialdried over MgSO4
filtrationfiltered off
customthe filtrate was evaporated
customThe residue was purified over silica with dichloromethane/methanol 95/5 as eluent

Sources & evidence

ORD record: ord-5a83c0033b024f4982759def2e69ff47
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09339494B2

Reaction notes

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