Water → (5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)(cyclobutyl)methanol

HRID 2204652Notes

Reaction equation

HRID 2204652 reaction equation
[CH:1]1([Mg]Br)[CH2:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[CH:13]=[N:12][C:11]2[NH:14][CH:15]=[CH:16][C:10]=2[C:9]=1[CH:17]=[O:18].O>C1COCC1>[Cl:7][C:8]1[C:9]([CH:17]([CH:1]2[CH2:4][CH2:3][CH2:2]2)[OH:18])=[C:10]2[CH:16]=[CH:15][NH:14][C:11]2=[N:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 242292805-Chloro-1H-pyrrolo[2,3-b]pyridine-4-carbaldehydeHCID 178419648HCID 178419648, compound

Product 1

HCID 58010144(5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)(cyclobutyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The solution of cyclobutylmagnesium bromide (0.28 M in THF, 56 mL, 63 mmol) was added to a solution of 5-chloro-1H-pyrrolo[2,3-b]pyridine-4-carbaldehyde (0.908 g, 5.03 mmol, Adesis) in THF (30 mL) at about 0° C. The reaction mixture was stirred and allowed to warm to ambient temperature and the reaction mixture was stirred for about 16 h. Water (10 mL) was added and the volatiles were removed under reduced pressure. The product was extracted into DCM (3×20 mL) and the combined organic phases were dried over anhydrous MgSO4, filtered, the solvent was removed under reduced pressure and the crude material was purified by column chromatography over silica gel using a 10 to 45% gradient of EtOAc in heptane as the eluent to provide (5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)(cyclobutyl)methanol as an off white solid (0.42 g, 32%); LC/MS (Table 2, Method a) Rt=2.02 min; m/z: 237 and 239 (M+H)+.

Workup

  1. stirringthe reaction mixture was stirred for about 16 h
  2. customthe volatiles were removed under reduced pressure
  3. extractionThe product was extracted into DCM (3×20 mL)
  4. dry with materialthe combined organic phases were dried over anhydrous MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customthe crude material was purified by column chromatography over silica gel using a 10 to 45% gradient of EtOAc in heptane as the eluent

Sources & evidence

ORD record
ord-2c39b212f6c5438ba5148a10d87f7f35
Source dataset
uspto-grants-2016_06
Patent number
US09365579B2

Reaction notes

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