3-Bromo-5-(trifluoromethyl)pyridine → 3,4-bis(Benzyloxy)-6-{2-[5-(trifluoromethyl)pyridin-3-yl]ethynyl}pyridazine

HRID 927084Notes

Reaction equation

HRID 927084 reaction equation
[CH2:1]([O:8][C:9]1[N:10]=[N:11][C:12]([C:23]#[C:24]C2C=CC(C(F)(F)F)=CN=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(C#C)=CC=1OCC1C=CC=CC=1)C1C=CC=CC=1.Br[C:60]1[CH:61]=[N:62][CH:63]=[C:64]([C:66]([F:69])([F:68])[F:67])[CH:65]=1>>[CH2:1]([O:8][C:9]1[N:10]=[N:11][C:12]([C:23]#[C:24][C:60]2[CH:61]=[N:62][CH:63]=[C:64]([C:66]([F:69])([F:68])[F:67])[CH:65]=2)=[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 111279913-Bromo-5-(trifluoromethyl)pyridineHCID 712699103,4-Bis(benzyloxy)-6-{[5-(trifluoromethyl)pyridin-2-yl]ethynyl}pyridazine2×HCID 866770253,4-Bis(benzyloxy)-6-ethynylpyridazine2×

Product 1

HCID 712703533,4-bis(Benzyloxy)-6-{2-[5-(trifluoromethyl)pyridin-3-yl]ethynyl}pyridazineYield 31%

Procedure

Prepared as described for 3,4-bis(benzyloxy)-6-{[5-(trifluoromethyl)pyridin-2-yl]ethynyl}pyridazine (Intermediate 6) from 3,4-bis(benzyloxy)-6-ethynylpyridazine (Intermediate 5) and 3-bromo-5-(trifluoromethyl)pyridine in 31% yield.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-b16278a8f7ab407f8891adb44fc68c89
Source dataset
uspto-grants-2016_03
Patent number
US09290456B2

Reaction notes

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