Ammonium Chloride → HCID 21106569, compound

HRID 1783723Notes

Reaction equation

HRID 1783723 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12]([Br:16])=[N:11][N:10]([CH:17]([CH3:19])[CH3:18])[C:9]2=[O:20])=O)C.[Li+].[BH4-].[NH4+].[Cl-]>C1COCC1>[Br:16][C:12]1[C:13]2[C:8](=[CH:7][C:6]([CH2:4][OH:3])=[CH:15][CH:14]=2)[C:9](=[O:20])[N:10]([CH:17]([CH3:19])[CH3:18])[N:11]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4148881Lithium borohydride2×HCID 68898772HCID 68898772, compound

Product 1

HCID 21106569HCID 21106569, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

1-Bromo-3-isopropyl-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid ethyl ester (2.3 g, 6.8 mmol) was suspended in THF (50 ml) and cooled to 0° C. To the suspension was added LiBH4 (5.1 ml of a 2M solution in THF, 10.2 mmol) dropwise, the suspension was allowed to warm to RT and stirred for 24 hours. After this time, LC-MS showed 50% starting material remained. To this was added LiBH4 (1.7 ml of a 2M solution in THF, 3.4 mmol) and the reaction mixture was stirred for a further 3 hours. The reaction was cooled to 0° C., saturated NH4Cl (40 ml) was added and the reaction mixture was then partitioned between water (50 ml) and DCM (150 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated under vacuum. The resulting residue was then purified by flash column chromatography (elution: 50% toluene, 30% EtOAc, 20% DCM) to give the title compound (0.9 g, 43% yield) as a white solid. δH (400 MHz, DMSO), 8.28 (1H, s), 7.96 (1H, d), 7.88 (1 H, d), 5.64 (1H, t), 5.31-5.18 (1H, m), 4.78 (2H, d), 1.35 (6H, d) Tr=1.31 min, m/z (ES+) (M+H)+ 297 & 299

Workup

  1. temperatureto warm to RT
  2. stirringwas stirred for a further 3 hours
  3. temperatureThe reaction was cooled to 0° C.
  4. customthe reaction mixture was then partitioned between water (50 ml) and DCM (150 ml)
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe resulting residue was then purified by flash column chromatography (elution: 50% toluene, 30% EtOAc, 20% DCM)

Sources & evidence

ORD record
ord-5dbfc16dfc15488b9359043baca91a64
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

Loading…