N-bromobutanimide → HCID 86727587, compound

HRID 519177Notes

Reaction equation

HRID 519177 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:21]=[C:20]2[C:11]([N:12]3[C:17]([CH2:18][O:19]2)=[N:16][NH:15][C:14](=[O:22])[C@H:13]3[CH3:23])=[CH:10][CH:9]=1.C1C(=O)N([Br:31])C(=O)C1>C(O)(C(F)(F)F)=O>[Br:31][C:9]1[CH:10]=[C:11]2[C:20](=[CH:21][C:8]=1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])[O:19][CH2:18][C:17]1[N:12]2[C@H:13]([CH3:23])[C:14](=[O:22])[NH:15][N:16]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 86727585HCID 86727585, compound

Product 1

HCID 86727587HCID 86727587, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of (R)-7-(2-fluoro-phenyl)-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (2.4 g, 7.71 mmol) in TFA (20 mL) was added NBS (1.37 g, 7.71 mmol) in portions. The reaction mixture was stirred at ambient temperature for 3 h then concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 10-50% EtOAc in petroleum ether) to give (R)-6-bromo-7-(2-fluoro-phenyl)-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (2.2 g, 73%) as a colorless solid. 1H NMR (400 MHz, CDCl3) δ 8.23 (brs, 1H), 7.45-7.36 (m, 1H), 7.30-7.11 (m, 5H), 6.99 (s, 1H), 4.74-4.69 (m, 1H), 4.69-4.55 (m, 2H), 1.58 (d, J=6.8 Hz, 3H).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was purified by column chromatography on silica gel (eluting with 10-50% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-b51c827682e4448fafcbda47d6c6ab76
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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