N-bromobutanimide → Tert-butyl 2-bromo-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepin-8-yl(tert-butyl)carbamate

HRID 628015Notes

Reaction equation

HRID 628015 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]([N:13]([C:21]1[N:31]=[CH:30][C:29]2[C:28]3[S:32][CH:33]=[CH:34][C:27]=3[CH2:26][CH2:25][O:24][C:23]=2[CH:22]=1)[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:12])([CH3:11])[CH3:10]>CN(C)C=O>[Br:1][C:33]1[S:32][C:28]2[C:29]3[CH:30]=[N:31][C:21]([N:13]([C:9]([CH3:10])([CH3:11])[CH3:12])[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:22][C:23]=3[O:24][CH2:25][CH2:26][C:27]=2[CH:34]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 57900224Tert-butyl tert-butyl(4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepin-8-yl)carbamate

Product 1

HCID 57900354Tert-butyl 2-bromo-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepin-8-yl(tert-butyl)carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of N-bromosuccinimide (59 mg, 0.33 mmol) in 1 ml of dimethylformamide was added dropwise to a solution of tert-butyl tert-butyl(4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepin-8-yl)carbamate (120 mg, 0.32 mmol) in 2 ml of dimethylformamide (DMF). The reaction mixture was stirred for 18 hours, concentrated in vacuum and partitioned between water and ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulfate and concentrated in vacuum to give tert-butyl 2-bromo-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepin-8-yl(tert-butyl)carbamate which was used in the next step without further purification. MS: (ESI+) 453.2

Workup

  1. concentrationconcentrated in vacuum
  2. custompartitioned between water and ethyl acetate
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-93c89c9813a74f5fbd89352c9e183a15
Source dataset
uspto-grants-2016_04
Patent number
US09309265B2

Reaction notes

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