Sodium Bicarbonate → HCID 59191510, compound

HRID 1479986Notes

Reaction equation

HRID 1479986 reaction equation
Cl[C:2]1[C:7]2[CH2:8][CH2:9][CH2:10][C:6]=2[C:5]([Cl:11])=[N:4][N:3]=1.[Br-].[CH2:13]([Zn+])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])(O)=O.[Na+]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:13]([C:2]1[C:7]2[CH2:8][CH2:9][CH2:10][C:6]=2[C:5]([Cl:11])=[N:4][N:3]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 154019081,4-dichloro-5H,6H,7H-cyclopenta[d]pyridazine2×HCID 178419772HCID 178419772, compound

Product 1

HCID 59191510HCID 59191510, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1,4-dichloro-6,7-dihydro-5H-cyclopenta[d]pyridazine (compound 39, 500 mg, 2.64 mmol) in THF (5 mL) is added Pd(PPh3)4 (383 mg, 0.33 mmol). The mixture is degassed and benzyl zinc bromide (11 mL, 0.5 M in THF, 5.6 mmol) is added. The mixture is heated at 60° C. for 5 h. The reaction mixture is cooled down to RT and saturated aq. NaHCO3 solution is added and the mixture is extracted with EtOAc. The combined orgaqnic layers are washed with water, brine, dried over NaSO4, filtered and concentrated. The crude product is purified by flash chromatography (EtOAc/heptane 10%-30%) to give compound 44 (490 mg, 76%).

Workup

  1. customThe mixture is degassed
  2. temperatureThe reaction mixture is cooled down to RT
  3. extractionthe mixture is extracted with EtOAc
  4. washThe combined orgaqnic layers are washed with water, brine
  5. dry with materialdried over NaSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product is purified by flash chromatography (EtOAc/heptane 10%-30%)

Sources & evidence

ORD record
ord-3d9d2d1276034f62af407f17a670dc3d
Source dataset
uspto-grants-2016_08
Patent number
US09409871B2

Reaction notes

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