HCID 67172060, compound → HCID 67170816, compound

HRID 1506362Notes

Reaction equation

HRID 1506362 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:24](=[CH:25][CH:26]=1)[C:8]1=[N:9][O:10][C:11]([C:12]3[CH:13]=[CH:14][C:15]([O:20][CH:21]([CH3:23])[CH3:22])=[C:16]([CH:19]=3)[C:17]#[N:18])=[C:7]1[CH2:6][CH2:5]2.[Br-].[CH2:28]([O:30][C:31](=[O:35])[CH2:32][CH2:33][Zn+])[CH3:29]>CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C.C1COCC1>[C:17]([C:16]1[CH:19]=[C:12]([C:11]2[O:10][N:9]=[C:8]3[C:24]4[C:4]([CH2:5][CH2:6][C:7]=23)=[CH:3][C:2]([CH2:33][CH2:32][C:31]([O:30][CH2:28][CH3:29])=[O:35])=[CH:26][CH:25]=4)[CH:13]=[CH:14][C:15]=1[O:20][CH:21]([CH3:23])[CH3:22])#[N:18]

Participants

5

Reactant 2

HCID 67172060HCID 67172060, compoundHCID 178471816HCID 178471816, compound

Product 1

HCID 67170816HCID 67170816, compound

Reagents, catalysts & solvents 2

HCID 178424406HCID 178424406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 5-(7-bromo-4,5-dihydronaphtho[1,2-c]isoxazol-3-yl)-2-isopropoxybenzonitrile (Preparation 15B, 0.1 g, 0.244 mmol) in a 2-dram vial was added THF (1 mL). The vial was purged with nitrogen gas for 3 min and (3-ethoxy-3-oxopropyl)zinc(II) bromide (0.5 M in THF) (0.977 mL, 0.489 mmol) was added followed by dichlorobis(tri-o-tolylphosphine)palladium(II) (1.921 mg, 2.443 μmol) at room temperature. The vial was again purged with nitrogen gas for 30 seconds and the pale yellow heterogeneous reaction mixture was stirred at room temperature for 18 h. To the reaction mixture was added potassium fluoride (60 mg) dissolved in 0.2 mL of water at room temperature. The contents were stirred at room temperature for 5 min. and then filtered. The solid was washed with ethyl acetate (2×5 mL). The filtrate was concentrated under reduced pressure to yield a pale yellow solid. LC/MS M+1=401.1.

Workup

  1. customThe vial was purged with nitrogen gas for 3 min
  2. customThe vial was again purged with nitrogen gas for 30 seconds
  3. additionTo the reaction mixture was added potassium fluoride (60 mg)
  4. dissolutiondissolved in 0.2 mL of water at room temperature
  5. stirringThe contents were stirred at room temperature for 5 min.
  6. filtrationfiltered
  7. washThe solid was washed with ethyl acetate (2×5 mL)
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customto yield a pale yellow solid

Sources & evidence

ORD record
ord-03c29340db524eaabba6ec94ee92f8cb
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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