HCID 86693077, compound → HCID 86693076, compound

HRID 575043Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][C:15]=1[F:16])[CH:12]1[CH2:17][CH:10]([CH2:11]1)[N:9]1[C:5]2=[N:6][C:7]([I:19])=[C:8]1I.CC[Mg+].[Br-]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][C:15]=1[F:16])[CH:12]1[CH2:11][CH:10]([CH2:17]1)[N:9]1[C:5]2=[N:6][C:7]([I:19])=[CH:8]1

Participants

Conditions

Temperature: -40 °C

Procedure

Into a 3000-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed a solution of 9-bromo-10-fluoro-3,4-diiodo-2,5-diazatetracyclo[11.1.1.0[2,6]. 0[7,12]]pentadeca-3,5,7,9,11-pentaene (252 g, 462.45 mmol, 1.00 equiv) in tetrahydrofuran (2000 mL), followed by the addition of EtMgBr (163 mL, 1.05 equiv, 3 M) dropwise with stirring at −40° C. over 30 min. The resulting solution was stirred at −40° C. for 30 min, quenched by the addition of 200 mL of NH4Cl (sat) and extracted with 2×1000 mL of ethyl acetate. The organic layers were combined, washed with 1×1000 mL of water and 1×1000 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to afford 173 g (89%) of 9-bromo-10-fluoro-4-iodo-2,5-diazatetracyclo[11.1.1.0[2,6].0[7,12]]pentadeca-3,5,7,9,11-pentaene as a red solid.

Workup

customInto a 3000-mL 4-necked round-bottom flask purged
temperaturemaintained with an inert atmosphere of nitrogen
stirringThe resulting solution was stirred at −40° C. for 30 min
customquenched by the addition of 200 mL of NH4Cl (sat)
extractionextracted with 2×1000 mL of ethyl acetate
washwashed with 1×1000 mL of water and 1×1000 mL of brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-0e64da3d51f647fd87333623c52d4f1c
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034866B2

Reaction notes

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