3,4-Bis(benzyloxy)-6-chloropyridazine → 3,4-bis(Benzyloxy)-6-[(2-chloro-6-fluorophenyl)methyl]pyridazine

HRID 927103Notes

Reaction equation

HRID 927103 reaction equation
[CH2:1]([O:8][C:9]1[N:10]=[N:11][C:12]([CH2:23]C2C=CC(F)=CC=2)=[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.[Cl-].[Cl:55][C:56]1[CH:63]=[CH:62][CH:61]=[C:60]([F:64])[C:57]=1C[Zn+]>>[CH2:1]([O:8][C:9]1[N:10]=[N:11][C:12]([CH2:23][C:57]2[C:60]([F:64])=[CH:61][CH:62]=[CH:63][C:56]=2[Cl:55])=[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

Participants

4

Reactant 3

HCID 122134743,4-Bis(benzyloxy)-6-chloropyridazine2×HCID 712704273,4-bis(Benzyloxy)-6-[(4-fluorophenyl)methyl]pyridazine2×HCID 178505703HCID 178505703, compound

Product 1

HCID 712700603,4-bis(Benzyloxy)-6-[(2-chloro-6-fluorophenyl)methyl]pyridazineYield 23%

Procedure

Prepared as described for 3,4-bis(benzyloxy)-6-[(4-fluorophenyl)methyl]pyridazine (Intermediate 51) from 3,4-bis(benzyloxy)-6-chloropyridazine (Intermediate 1) and (2-chloro-6-fluorobenzyl)zinc(II) chloride in 23% yield.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-301468c5c9fe41f7ac9ead2fd9499fe6
Source dataset
uspto-grants-2016_03
Patent number
US09290456B2

Reaction notes

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