HCID 66674804, compound → HCID 59726023, compound

HRID 422572Notes

Reaction equation

HRID 422572 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]([CH3:25])=[C:6]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[C:14]([O:18][C@H:19]([CH3:24])[C:20]([F:23])([F:22])[F:21])=[N:13][N:12]=[CH:11]3)[CH:7]=1.[Cu](C#N)[C:27]#[N:28]>CN(C=O)C.C(Cl)Cl>[CH3:25][C:5]1[CH:4]=[CH:3][C:2]([C:27]#[N:28])=[CH:7][C:6]=1[C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[C:14]([O:18][C@H:19]([CH3:24])[C:20]([F:21])([F:22])[F:23])=[N:13][N:12]=[CH:11]2

Participants

5

Reactant 2

HCID 66674804HCID 66674804, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 59726023HCID 59726023, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 6-(5-iodo-2-methylphenyl)-1-((R)-1,1,1-trifluoropropan-2-yloxy)phthalazine (100 mg, 0.22 mmol) and copper cyanide (98 mg, 1.09 mmol) in 1.0 mL of DMF in a sealed glass tube was heated at 120° C. in a microwave synthesizer for 20 min. The cooled reaction was diluted with CH2Cl2 and washed with water and brine. The organic layer was dried (MgSO4), filtered, and concentrated. Purification on a silica gel column (20-50% of EtOAc in Hexanes) afforded 4-methyl-3-(1-((R)-1,1,1-trifluoropropan-2-yloxy)phthalazin-6-yl)benzonitrile as a white solid. MS (ESI, pos. ion) m/z: 358.4 (M+1).

Workup

  1. customThe cooled reaction
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification on a silica gel column (20-50% of EtOAc in Hexanes)

Sources & evidence

ORD record
ord-738b13156af74d218ea72ab927e2ad89
Source dataset
uspto-grants-2012_01
Patent number
US08101612B2

Reaction notes

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