Phenol → HCID 58119008, compound

HRID 406438Notes

Reaction equation

HRID 406438 reaction equation
C1(O)C=CC=CC=1.[F:8][C:9]([F:27])([F:26])[C:10]1[N:14]2[CH:15]=[C:16]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)[CH:17]=[CH:18][C:13]2=[N:12][N:11]=1.BrC1C=N[C:32]2N([C:35]([CH:38]([CH3:40])C)=[N:36][N:37]=2)C=1.C([O-])([O-])=O.[Cs+].[Cs+].C(#N)CCC>>[N:37]1[CH:32]=[CH:40][CH:38]=[C:35]([O:25][C:22]2[CH:21]=[CH:20][C:19]([C:16]3[CH:17]=[CH:18][C:13]4[N:14]([C:10]([C:9]([F:8])([F:26])[F:27])=[N:11][N:12]=4)[CH:15]=3)=[CH:24][CH:23]=2)[N:36]=1

Participants

6

Reactant 5

HCID 996PhenolHCID 8008ButyronitrileHCID 10796Cesium carbonateHCID 58118934HCID 58118934, compoundHCID 58118986HCID 58118986, compound

Product 1

HCID 58119008HCID 58119008, compound

Conditions

Temperature
140 °C

Procedure

In a sealable flask, a suspension of the phenol, 4-(3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)phenol, prepared as described in Example 1 (47 mg, 0.17 mmol), heteroaryl chloride (39 mg, 0.34 mmol), Cs2CO3 (111 mg, 0.34 mmol), and butyronitrile (1 mL) is heated to 140° C. overnight. The reaction is concentrated and purified by RP-HPLC to afford the desired product, 6-(4-(pyridazin-3-yloxy)phenyl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine.

Workup

  1. customprepared
  2. concentrationThe reaction is concentrated
  3. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-16749065b32e4c269868dcff6895e94b
Source dataset
uspto-grants-2014_06
Patent number
US08754103B2

Reaction notes

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