N-bromobutanimide → HCID 66604304, compound

HRID 2410894Notes

Reaction equation

HRID 2410894 reaction equation
[F:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:15]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[O:16])[CH:12]=3)[NH:7][C:6]=2[C:5]([C:23]([NH2:25])=[O:24])=[CH:4][CH:3]=1.C1C(=O)N([Br:33])C(=O)C1>CN(C=O)C>[Br:33][C:3]1[CH:4]=[C:5]([C:23]([NH2:25])=[O:24])[C:6]2[NH:7][C:8]3[C:13]([C:14]=2[C:2]=1[F:1])=[CH:12][C:11]([C:15]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[O:16])=[CH:10][CH:9]=3

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 66604445HCID 66604445, compound

Product 1

HCID 66604304HCID 66604304, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-Fluoro-6-(morpholine-4-carbonyl)-9H-carbazole-1-carboxamide (9 mg, 0.026 mmol) was mixed with NBS (5.5 mg, 0.031 mmol) in DMF (1.5 mL). The mixture was stirred at 80° C. for 20 mins More NBS (3 mg, 0.017 mmol) was added to the mixture and heated at 80° C. for another 20 mins. The mixture was concentrated and purified using preparative HPLC to give 3-bromo-4-fluoro-6-(morpholine-4-carbonyl)-9H-carbazole-1-carboxamide. MS (ESI) m/z 420 (M+H)+. 1H NMR (DMSO-d6) δ ppm 11.72 (s, 1H), 8.32 (d, 1H, J=6.5), 8.28 (bs, 1H), 8.13 (s, 1H), 7.85(d, 1H, J=8.3), 7.64 (bs, 1H), 7.58(dd, 1H, J=8.5, 1.6), 3.7-3.5 (bm, 8H).

Workup

  1. additionwas added to the mixture
  2. concentrationThe mixture was concentrated
  3. custompurified

Sources & evidence

ORD record
ord-2e228626585445659f87e8c76cf25642
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

Loading…