Water → (Rac)-2-[(8-bromo-2,3,5,6-tetrahydro[1,4]oxazino-[2,3,4-hi]indol-6-yl)methyl]-1h-isoindole-1,3(2h)-dione

HRID 2179904Notes

Reaction equation

HRID 2179904 reaction equation
[O:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]([CH2:13][N:14]2[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15]2=[O:24])[CH2:5][N:4]3[CH2:3][CH2:2]1.[Br:25]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:25][C:9]1[CH:8]=[C:7]2[C:12]3=[C:11]([O:1][CH2:2][CH2:3][N:4]3[CH2:5][CH:6]2[CH2:13][N:14]2[C:22](=[O:23])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:24])[CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 22488989(Rac)-2-(2,3,5,6-tetrahydro[1,4]oxazino[2,3,4-hi]indol-6-ylmethyl)-1h-isoindole-1,3(2h)-dione

Product 1

HCID 20778787(Rac)-2-[(8-bromo-2,3,5,6-tetrahydro[1,4]oxazino-[2,3,4-hi]indol-6-yl)methyl]-1h-isoindole-1,3(2h)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (rac)-2-(2,3,5,6-tetrahydro[1,4]oxazino[2,3,4-hi]indol-6-ylmethyl)-1H-isoindole-1,3(2H)-dione (0.030 g, 0.094 mmol) in DMF (1.0 mL) was added the solution of N-bromosuccinimide (0.018 g, 0.098 mmol). The reaction mixture was stirred at room temperature for 1 hour and water (10.0 mL) was added. The aqueous solution was extracted with EtOAc (3×) and the combined EtOAc solution was dried over MgSO4 and filtered. The filtrate was concentrated in vacuo to dryness to give 0.035 g (94%) of light yellow oil as the desired product: 1H NMR (400 MHz, CDCl3) δ 7.82-7.79 (m, 2 H), 7.70-7.63 (m, 2 H), 6.81 (s, 1 H), 6.70 (s, 1 H), 4.34-4.29 (m, 2 H), 3.93-3.81 (m, 2 H), 3.63-3.59 (m, 1 H), 3.27-3.23 (m, 1 H), 3.19-3.15 (m, 1 H), 3.05-3.00 (m, 1 H), 2.98-2.89 (m, 1 H); MS (EI) m/z 399 (M++H), 401 (M++H).

Workup

  1. extractionThe aqueous solution was extracted with EtOAc (3×)
  2. dry with materialthe combined EtOAc solution was dried over MgSO4
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-a9bd0eb40daa4ced9a18eb3af1035a38
Source dataset
uspto-grants-2005_05
Patent number
US06887868B2

Reaction notes

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