2-Bromoethanol → 6-[4-[4-(2-Bromoethoxy)phenyl]piperazin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine

HRID 1675151Notes

Reaction equation

CC(OC(/N=N/C(OC(C)C)=O)=O)C.[F:15][C:16]([F:40])([F:39])[C:17]1[N:21]2[N:22]=[C:23]([N:26]3[CH2:31][CH2:30][N:29]([C:32]4[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=4)[CH2:28][CH2:27]3)[CH:24]=[CH:25][C:20]2=[N:19][N:18]=1.[Br:41][CH2:42][CH2:43]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Br:41][CH2:42][CH2:43][O:38][C:35]1[CH:36]=[CH:37][C:32]([N:29]2[CH2:28][CH2:27][N:26]([C:23]3[CH:24]=[CH:25][C:20]4[N:21]([C:17]([C:16]([F:15])([F:39])[F:40])=[N:18][N:19]=4)[N:22]=3)[CH2:31][CH2:30]2)=[CH:33][CH:34]=1

Participants

Conditions

Temperature: 20 °C

Procedure

DIAD (1.625 mL, 8.25 mmol) was added to 4-[4-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperazin-1-yl]phenol (obtained as described in Example 514, preparation of starting materials) (3.01 g, 8.25 mmol), 2-bromoethanol (0.645 mL, 9.08 mmol) and triphenylphosphine (2.165 g, 8.25 mmol) in THF (150 mL) at 20° C. under nitrogen. The resulting solution was stirred at 20° C. for 16 hours. The crude product was purified by flash silica chromatography, elution gradient 0 to 3% MeOH in DCM to afford 6-[4-[4-(2-bromoethoxy)phenyl]piperazin-1-yl]-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (0.765 g, 19.67%) as a pale yellow solid.

Workup

customThe crude product was purified by flash silica chromatography, elution gradient 0 to 3% MeOH in DCM

Sources & evidence

ORD record: ord-dbd93fb08cc347b991c7b1b17cd67d5f
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003649B2

Reaction notes

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