Cesium carbonate → HCID 71235283, compound

HRID 1483860Notes

Reaction equation

HRID 1483860 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=3)=[N:9][N:10]=2)[CH:7]=1.[O:21]1[CH2:26][CH2:25][CH:24]([NH2:27])[CH2:23][CH2:22]1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[O:21]1[CH2:26][CH2:25][CH:24]([NH:27][C:2]2[CH:3]=[CH:4][C:5]3[N:6]([C:8]([C:11]4[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=4)=[N:9][N:10]=3)[CH:7]=2)[CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 4192234-AminotetrahydropyranHCID 634876Binap, (A+-)-HCID 71227653HCID 71227653, compound

Product 1

HCID 71235283HCID 71235283, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a suspension of 6-iodo-3-(3-(trifluoromethyl)phenyl)-[1,2,4]triazolo[4,3-a]pyridine (0.101 g, 0.26 mmol) and tetrahydro-2H-pyran-4-amine (0.131 g, 1.30 mmol) in toluene (1 mL) was added rac-Binap (0.049 g, 0.078 mmol), Pd(OAc)2 (0.012 g, 0.052 mmol) and Cs2CO3 (0.169 g, 0.52 mmol). It was flushed with argon then heated at 110° C. overnight. It was absorbed on SiO2 and purified on column chromatography on SiO2 with 60% 15% MeOH/EA in hexane. This product was further purified on C18 column chromatography using 20-40% ACN in water.

Workup

  1. customIt was flushed with argon
  2. customIt was absorbed on SiO2
  3. custompurified on column chromatography on SiO2 with 60% 15% MeOH/EA in hexane
  4. customThis product was further purified on C18 column chromatography

Sources & evidence

ORD record
ord-b738c0065c7e4ea995af3260e7ccc5bb
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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