Bromine → tert-butyl 4-(3-(2-bromoacetyl)-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl)-1,4-diazepane-1-carboxylate

HRID 2206337Notes

Reaction equation

HRID 2206337 reaction equation
[C:1]([C:4]1[C:27](=[O:28])[O:26][C:7]2=[N:8][C:9]([N:12]3[CH2:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][CH2:13]3)=[CH:10][CH:11]=[C:6]2[CH:5]=1)(=[O:3])[CH3:2].[Br:29]Br>C(Cl)(Cl)Cl>[Br:29][CH2:2][C:1]([C:4]1[C:27](=[O:28])[O:26][C:7]2=[N:8][C:9]([N:12]3[CH2:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:14][CH2:13]3)=[CH:10][CH:11]=[C:6]2[CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 89783253tert-butyl 4-(3-acetyl-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl)-1,4-diazepane-1-carboxylate

Product 1

HCID 89793974tert-butyl 4-(3-(2-bromoacetyl)-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl)-1,4-diazepane-1-carboxylateYield 32%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

tert-Butyl 4-(3-acetyl-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl)-1,4-diazepane-1-carboxylate (350 mg, 0.903 mmol) in 10 mL of chloroform was treated with bromine (1M in CHCl3, 0.9 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16 hours. The precipitated solid was filtered and the mother liquor was concentrated. The residue was purified on silica gel to yield tert-butyl 4-(3-(2-bromoacetyl)-2-oxo-2H-pyrano[2,3-b]pyridin-7-yl)-1,4-diazepane-1-carboxylate (132.2 mg, 32%). MS m/z 489 [M+Na]+.

Workup

  1. filtrationThe precipitated solid was filtered
  2. concentrationthe mother liquor was concentrated
  3. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-10446a3388ea4a54ba271280a9a7cf7e
Source dataset
uspto-grants-2016_06
Patent number
US09371336B2

Reaction notes

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