HCID 178495872, compound → HCID 86693073, compound

HRID 575041Notes

Reaction equation

HRID 575041 reaction equation
[Br:1][C:2]1[CH:12]=[C:11]2[C:5]([CH:6]3[CH2:20][CH:8]([N:9]=[C:10]2[NH:13][CH2:14][CH:15](OC)OC)[CH2:7]3)=[CH:4][C:3]=1[F:21]>Cl>[Br:1][C:2]1[CH:12]=[C:11]2[C:5](=[CH:4][C:3]=1[F:21])[CH:6]1[CH2:20][CH:8]([CH2:7]1)[N:9]1[C:10]2=[N:13][CH:14]=[CH:15]1

Participants

3

Reactant 1

HCID 178495872HCID 178495872, compound

Product 1

HCID 86693073HCID 86693073, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
90 °C

Procedure

Into a 3000-mL 4-necked round-bottom flask was placed a solution of 5-bromo-N-(2,2-dimethoxyethyl)-4-fluoro-9-azatricyclo[8.1.1.0[2,7]]dodeca-2,4,6,8-tetraen-8-amine (350 g, 979.79 mmol, 1.00 equiv) in hydrogen chloride (3M) (1500 mL). The resulting solution was stirred at 90° C. for 90 min and extracted with 1×1000 mL of ethyl acetate. The pH value of the aqueous layer was adjusted to 10 with sodium hydroxide (3 mol/L). The resulting solution was extracted with 3×500 mL of ethyl acetate. The organic layers were combined and concentrated under vacuum. The residue was applied onto a silica gel column eluting with ethyl acetate: petroleum ether (1:2) to afford 150 g (52%) of 9-bromo-10-fluoro-2,5-diazatetracyclo[11.1.1.0[2,6].0[7,12]]pentadeca-3,5,7,9,11-pentaene as a white solid.

Workup

  1. customInto a 3000-mL 4-necked round-bottom flask was placed
  2. extractionextracted with 1×1000 mL of ethyl acetate
  3. extractionThe resulting solution was extracted with 3×500 mL of ethyl acetate
  4. concentrationconcentrated under vacuum
  5. washeluting with ethyl acetate: petroleum ether (1:2)

Sources & evidence

ORD record
ord-00846fc832dd436bba56001a55dcce07
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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