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

HRID 1854500Notes

Reaction equation

HRID 1854500 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-261b3d0200e04136aa8be279976d1fc8
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

Loading…