Diisopropylethylamine → HCID 86685247, compound

HRID 522890Notes

Reaction equation

HRID 522890 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](F)[N:3]=1.C(N(C(C)C)C(C)C)C.Cl.[F:19][C:20]1[CH:30]=[CH:29][C:23]([O:24][CH:25]2[CH2:28][NH:27][CH2:26]2)=[CH:22][CH:21]=1>CC(O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:27]2[CH2:28][CH:25]([O:24][C:23]3[CH:22]=[CH:21][C:20]([F:19])=[CH:30][CH:29]=3)[CH2:26]2)[N:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6394382-Bromo-6-fluoropyridineHCID 214287323-(4-Fluorophenoxy)azetidine hydrochloride

Product 1

HCID 86685247HCID 86685247, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To 2-bromo-6-fluoropyridine (150.0 mg, 0.852 mmol) in 2-propanol (3.00 mL) at RT was added N-ethyl-N-isopropylpropan-2-amine (0.445 mL, 2.56 mmol) followed by 3-(4-fluorophenoxy)azetidine hydrochloride (174 mg, 0.852 mmol). The resulting reaction mixture was stirred at RT for 3.5 h, then heated to 70° C. for 24 h, cooled to RT and concentrated. Purification of the crude product using MPLC (5 g cartridge, 12 g column, 0 to 60% EtOAc-hexanes) gave 2-bromo-6-(3-(4-fluorophenoxy)azetidin-1-yl)pyridine (211.4 mg).

Workup

  1. customThe resulting reaction mixture
  2. temperatureheated to 70° C. for 24 h
  3. temperaturecooled to RT
  4. concentrationconcentrated
  5. customPurification of the crude product

Sources & evidence

ORD record
ord-b255fd59b76541e8b43bdbf37b669088
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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