Diethyl Ether → HCID 67061210, compound

HRID 2234549Notes

Reaction equation

HRID 2234549 reaction equation
N[C:2]1[C:7]([CH:8]=[O:9])=[CH:6][C:5]([Br:10])=[CH:4][N:3]=1.[CH3:11][Mg]Br.C(O[CH2:17][CH3:18])C.[Cl-].[NH4+].[CH2:21]1[CH2:25]OC[CH2:22]1>>[NH2:3][C:2]1[CH:11]=[CH:4][C:5]([Br:10])=[CH:6][C:7]=1[CH:8]([CH:18]1[CH2:17][CH2:25][CH2:21][CH2:22]1)[OH:9]

Participants

6

Reactant 5

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 242137922-Amino-5-bromo-3-pyridinecarbaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 67061210HCID 67061210, compoundYield 50%

Procedure

To a solution of 2-Amino-5-bromo-pyridine-3-carbaldehyde (632 mg, 3.14 mmol) in anhydrous THF (20 mL) was methylmagnesium bromide 3M in diethyl ether (6.06 mL, 34.8 mmol) is added at −50° C. The reaction mixture was warmed to room temperature and stirred overnight. Saturated aqueous ammonium chloride was added to the mixture (15 mL), the organic layer separated and the aqueous phase extracted with EtOAc (3×20 mL). Organic layers were dried over sodium sulfate, filtered and concentrated. The crude residue was purified by flash silica chromatography with a gradient of ethyl acetate in hexanes. (2-Amino-5-bromo-phenyl)-cyclopentyl-methanol (425.9 mg, 50% yield) was obtained as a yellow powder. MS: m/z 271/273 [MH+].

Workup

  1. additionis added at −50° C
  2. customthe organic layer separated
  3. extractionthe aqueous phase extracted with EtOAc (3×20 mL)
  4. dry with materialOrganic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by flash silica chromatography with a gradient of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-6d1cb279ac9441c5a79354963fcf0372
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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