Diisopropylethylamine → 1-(6-Bromopyridin-2-yl)-1,4-diazepan-6-ol

HRID 57897

Reaction equation

HRID 57897 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](F)[N:3]=1.[NH:9]1[CH2:15][CH:14]([OH:16])[CH2:13][NH:12][CH2:11][CH2:10]1.CCN(C(C)C)C(C)C>C(O)C>[Br:1][C:2]1[N:3]=[C:4]([N:9]2[CH2:15][CH:14]([OH:16])[CH2:13][NH:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6394382-Bromo-6-fluoropyridineHCID 211142751,4-Diazepan-6-ol

Product 1

HCID 867070881-(6-Bromopyridin-2-yl)-1,4-diazepan-6-olYield 54.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromo-6-fluoropyridine (477 mg, 2.7 mmol), 1,4-diazepan-6-ol (350 mg, 3 mmol), and DIPEA (1.94 g, 15 mmol) in ethanol (10 mL) was heated at 100° C. for 16 hours. After it was cooled, the reaction mixture was concentrated under reduced pressure. The residue was diluted with EtOAc (100 mL) and washed with brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford 1-(6-bromopyridin-2-yl)-1,4-diazepan-6-ol as a colorless oil (400 mg, 48.9%). MS (ESI) m/z: 272 [M+H]+.

Workup

  1. temperatureAfter it was cooled
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionThe residue was diluted with EtOAc (100 mL)
  4. washwashed with brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4a05fc6b800647e6bfba96bdba62fac7
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Linked notes

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