3,4-Bis(benzyloxy)-6-chloropyridazine → 3,4-bis(Benzyloxy)-6-[(E)-2-[3,5-bis(trifluoromethyl)phenyl]-ethenyl]pyridazine

HRID 927120Notes

Reaction equation

HRID 927120 reaction equation
C(OC1N=NC(C(C2C=CC=CC=2)=C)=CC=1OCC1C=CC=CC=1)C1C=CC=CC=1.[CH2:31]([O:38][C:39]1[N:40]=[N:41][C:42](Cl)=[CH:43][C:44]=1[O:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[F:54][C:55]([F:78])([F:77])[C:56]1[CH:57]=[C:58](/[CH:66]=[CH:67]/B2OC(C)(C)C(C)(C)O2)[CH:59]=[C:60]([C:62]([F:65])([F:64])[F:63])[CH:61]=1>>[CH2:31]([O:38][C:39]1[N:40]=[N:41][C:42](/[CH:67]=[CH:66]/[C:58]2[CH:59]=[C:60]([C:62]([F:63])([F:65])[F:64])[CH:61]=[C:56]([C:55]([F:54])([F:77])[F:78])[CH:57]=2)=[CH:43][C:44]=1[O:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 3

HCID 122134743,4-Bis(benzyloxy)-6-chloropyridazine2×HCID 162181902-{(E)-2-[3,5-Bis(trifluoromethyl)phenyl]ethenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 86677027HCID 86677027, compound2×

Product 1

HCID 866770353,4-bis(Benzyloxy)-6-[(E)-2-[3,5-bis(trifluoromethyl)phenyl]-ethenyl]pyridazineYield 77%

Procedure

Prepared as described for 3,4-bis(benzyloxy)-6-(1-phenylethenyl)pyridazine (Intermediate 25) from 3,4-bis(benzyloxy)-6-chloropyridazine (Intermediate 1) and 2-[(E)-2-[3,5-bis(trifluoromethyl)phenyl]ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in 77% yield.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-eea7a35801384681b1e27b46a9e2e557
Source dataset
uspto-grants-2016_03
Patent number
US09290456B2

Reaction notes

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