N-bromobutanimide → HCID 66671334, compound

HRID 1505633Notes

Reaction equation

HRID 1505633 reaction equation
[CH2:1]([NH:8][C:9]1[C:14]2[C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)=[CH:16][S:17][C:13]=2[CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:25]N1C(=O)CCC1=O>C1COCC1>[CH2:1]([NH:8][C:9]1[C:14]2[C:15]([C:18]3[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=3)=[CH:16][S:17][C:13]=2[C:12]([Br:25])=[CH:11][N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 16222885HCID 16222885, compound

Product 1

HCID 66671334HCID 66671334, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl-(3-p-tolyl-thieno[3,2-c]pyridin-4-yl)-amine (314 mg, 0.984 mmol), in THF (5 ml) cooled to 0° C., was added N-bromosuccinimide (168 mg, 0.984 mmol) and the reaction stirred for 1.5 h. The reaction was then allowed to warm to room temperature and the solvent removed in vacuo. The crude residue was partitioned between NH4Cl (25 ml) and DCM (10 ml), the organic layer dried (MgSO4) and the solvent removed in vacuo. No further purification was required. The product was obtained as a yellow solid (390 mg, quantitative).

Workup

  1. customthe solvent removed in vacuo
  2. customThe crude residue was partitioned between NH4Cl (25 ml) and DCM (10 ml)
  3. dry with materialthe organic layer dried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customNo further purification
  6. customThe product was obtained as a yellow solid (390 mg, quantitative)

Sources & evidence

ORD record
ord-33c73a17f484458ea95b45238745f536
Source dataset
uspto-grants-2015_12
Patent number
US09216992B2

Reaction notes

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