Water → 2-Bromo-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepine

HRID 84466Notes

Reaction equation

HRID 84466 reaction equation
[Br:1]N1C(=O)CCC1=O.[S:9]1[C:13]2[C:14]3[CH:22]=[N:21][CH:20]=[CH:19][C:15]=3[O:16][CH2:17][CH2:18][C:12]=2[CH:11]=[CH:10]1.O>CN(C)C=O>[Br:1][C:10]1[S:9][C:13]2[C:14]3[CH:22]=[N:21][CH:20]=[CH:19][C:15]=3[O:16][CH2:17][CH2:18][C:12]=2[CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 579001994,5-Dihydropyrido[4,3-b]thieno[2,3-d]oxepine

Product 1

HCID 579000912-Bromo-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepineYield 65.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N-Bromosuccinimide (0.237 g, 1.33 mmol) in dimethylformamide (4 mL) was added dropwise to a solution of 4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepine (0.250 g, 1.23 mmol) in dimethylformamide (4 mL, 100 mmol) at 0° C. The reaction mixture was stirred for 18 hours at room temperature. The reaction mixture was mixed with 40 ml of water and extracted with 20 ml of ethylacetate twice. Combined organic extracts were washed with water and brine, and dried over MgSO4. The solvent was evaporated affording 2-bromo-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepine (0.227 g, 63%). 1H NMR (500 MHz, CDCl3) 8.76 (s, 1H), 8.26 (d, J=5.4, 1H), 6.90 (d, J=5.5, 1H), 6.88 (s, 1H), 4.36 (t, J=4.7, 2H), 3.19 (t, J=4.8, 2H). MS (ESI+) 282.0

Workup

  1. extractionextracted with 20 ml of ethylacetate twice
  2. washCombined organic extracts were washed with water and brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-213476a895a04bf08c0233c3f51e62c8
Source dataset
uspto-grants-2014_09
Patent number
US08846762B2

Reaction notes

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