Diisopropylethylamine → 1-(3-Bromo-6-iodopyridin-2-yl)-1,4-diazepan-6-ol

HRID 57977Notes

Reaction equation

HRID 57977 reaction equation
[Br:1][C:2]1[C:3](F)=[N:4][C:5]([I:8])=[CH:6][CH:7]=1.[NH:10]1[CH2:16][CH:15]([OH:17])[CH2:14][NH:13][CH2:12][CH2:11]1.CCN(C(C)C)C(C)C>CCO>[Br:1][C:2]1[C:3]([N:10]2[CH2:16][CH:15]([OH:17])[CH2:14][NH:13][CH2:12][CH2:11]2)=[N:4][C:5]([I:8])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 211142751,4-Diazepan-6-olHCID 717430873-Bromo-2-fluoro-6-iodopyridine

Product 1

HCID 867071591-(3-Bromo-6-iodopyridin-2-yl)-1,4-diazepan-6-olYield 87.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-bromo-2-fluoro-6-iodopyridine (1.00 g, 3.4 mmol), 1,4-diazepan-6-ol (510 mg, 4.4 mmol), and DIPEA (2 mL) in EtOH (6 mL) in a sealed tube was stirred at 100° C. for 20 hours. The reaction mixture was concentrated under reduced pressure to give a residue (1.18 g), which was used for the next step without further purification. MS (ESI) m/z: 398 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-430b14e236a94fdb91f5f889ce24ada9
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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