N-bromobutanimide → HCID 67298644, compound

HRID 1008991Notes

Reaction equation

HRID 1008991 reaction equation
[Br:1]N1C(=O)CCC1=O.[F:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[C:16]1[C:17]2[S:28][C:27]([C:29]([O:31][CH3:32])=[O:30])=[CH:26][C:18]=2[N:19]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:20]=1>C(Cl)Cl>[Br:1][C:20]1[N:19]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[C:18]2[CH:26]=[C:27]([C:29]([O:31][CH3:32])=[O:30])[S:28][C:17]=2[C:16]=1[CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH:10]1[F:9]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67298580methyl 6-(2-fluorocyclohexyl)-4-(2-methoxy-2-oxoethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate

Product 1

HCID 67298644HCID 67298644, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-bromo succinimide (1.5 eq.) was added at 0° C. to a 0.1M solution of methyl 6-(2-fluorocyclohexyl)-4-(2-methoxy-2-oxoethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate in dry DCM, and the mixture was stirred for 1 h. After dilution with EtOAc, the organic layer was washed with aq. Na2S2O3-solution and brine, dried over Na2SO4 and concentrated i. vac. Yield: 100%. 1H-NMR (300 MHz, CDCl3, 300 K, δ) 7.58 (s, 1H), 4.88 (d, 1H, J 17.9), 4.79 (d, 1H, J 17.9), 4.64 (dtd, 1H, J 49.3, 10.6, 4.4), 3.88 (s, 3H), 3.78 (s, 3H), 2.94-2.83 (m, 1H), 2.28-2.24 (m, 1H), 1.99-1.33 (m, 7H); MS (ES+) m/z 432, 434 (M+H)+.

Workup

  1. washAfter dilution with EtOAc, the organic layer was washed with aq. Na2S2O3-solution and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated i

Sources & evidence

ORD record
ord-59cf6526498d4e30b78458d9c09d483c
Source dataset
uspto-grants-2011_07
Patent number
US07973026B2

Reaction notes

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