Hydroxylamine → HCID 3013464, compound

HRID 722123Notes

Reaction equation

HRID 722123 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[C:3]([C:14]([O:16]CC)=O)[N:2]=1.[H-].[Na+].[F:21][C:22]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:23]=1[CH2:24]Br.[NH2:31][OH:32]>CN(C=O)C.CO.O>[F:21][C:22]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:23]=1[CH2:24][N:12]1[C:13]2[CH:1]=[N:2][C:3]([C:14]([NH:31][OH:32])=[O:16])=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

8

Reactant 4

HCID 787HydroxylamineHCID 24758Sodium hydrideHCID 902971-(Bromomethyl)-2,4-difluorobenzeneHCID 105078Ethyl Beta-Carboline-3-Carboxylate

Product 1

HCID 3013464HCID 3013464, compoundYield 37%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of ethyl 9H-β-carboline-3-carboxylate (370 mg, 1.54 mmol) in DMF (5 mL) under a nitrogen atmosphere was added NaH (61.6 mg, 60% in mineral oil, 1.54 mmol) portionwise, followed by 2,4-difluorobenzyl bromide (198 μL, 1.54 mmol). Stirring was continued for 48 hours at ambient temperature, water (100 mL) was then added to the mixture. The precipitate was filtered, washed with water and dried to give a solid that was dissolved in methanol (35 mL). To the resulting solution, H2NOH (30 mL, 50 wt. % solution in H2O, 0.45 mol) was added. The suspension was stirred for 4 days at ambient temperature. The mixture was then filtered, and the solid was recrystallized from methanol to give the title product (0.20 g, 37%). 1H NMR (400 MHz, DMSO-d6): δ 11.46 (1H, s), 9.15–9.22 (2H, m), 9.02 (1H, s), 8.64 (1H, d, J=8 Hz), 7.15–7.96 (6H, m), 6.06 (2H, s). HRMS (M+H)+ found: 354.1062. Calcd for C19H14F2N3O2FCl: 354.1054.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried
  4. customto give a solid
  5. stirringThe suspension was stirred for 4 days at ambient temperature
  6. filtrationThe mixture was then filtered
  7. customthe solid was recrystallized from methanol

Sources & evidence

ORD record
ord-4a6781c35bea48b69fd4612ce58f04f5
Source dataset
uspto-grants-2006_11
Patent number
US07138408B2

Reaction notes

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