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

HRID 627893Notes

Reaction equation

HRID 627893 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) δ 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-48c1d1002cc34fddb4ff3b6f431aef09
Source dataset
uspto-grants-2016_04
Patent number
US09309265B2

Reaction notes

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