3,4-Bis(benzyloxy)-6-chloropyridazine → HCID 86677034, compound

HRID 927116Notes

Reaction equation

HRID 927116 reaction equation
[CH2:1]([O:8][C:9]1[N:10]=[N:11][C:12]([C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH2:24])=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC1N=NC(Cl)=CC=1OCC1C=CC=CC=1)C1C=CC=CC=1.CC1(C)C(C)(C)OB(C(C2C=CC([C:70]([F:73])([F:72])[F:71])=CC=2)=C)O1>>[CH2:1]([O:8][C:9]1[N:10]=[N:11][C:12]([C:23]([C:25]2[CH:30]=[CH:29][C:28]([C:70]([F:73])([F:72])[F:71])=[CH:27][CH:26]=2)=[CH2:24])=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 122134743,4-Bis(benzyloxy)-6-chloropyridazine2×HCID 86677027HCID 86677027, compound2×HCID 866770324-Trifluoromethyl-1-phenylvinylboronic acid pinacol ester2×

Product 1

HCID 86677034HCID 86677034, compoundYield 48%

Procedure

Prepared according to the method for 3,4-bis(benzyloxy)-6-(1-phenylethenyl)pyridazine (Intermediate 25) from 3,4-bis(benzyloxy)-6-chloropyridazine (Intermediate 1) and 4,4,5,5-tetramethyl-2-{1-[4-(trifluoromethyl)-phenyl]ethenyl}-1,3,2-dioxaborolane (Intermediate 66) in 48% yield.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-c8827ba687c04b40bc388f70523bc1cc
Source dataset
uspto-grants-2016_03
Patent number
US09290456B2

Reaction notes

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