1,1,1-Trifluoro-2-propanamine → HCID 118271714, compound

HRID 590788Notes

Reaction equation

HRID 590788 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8](I)=[N:9][N:10]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:4]=2[CH:3]=1.[F:31][C:32]([F:37])([F:36])[CH:33]([NH2:35])[CH3:34].CC(C)([O-])C.[Na+]>C1COCC1.CC(C1C=C(C(C)C)C(C2C(P(C(C)(C)C)C(C)(C)C)=CC=CC=2)=C(C(C)C)C=1)C.C1C=[C-]C(CCN)=CC=1.Cl[Pd+]>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([NH:35][CH:33]([CH3:34])[C:32]([F:37])([F:36])[F:31])=[N:9][N:10]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 37831651,1,1-Trifluoro-2-propanamineHCID 23676156Sodium t-butoxideHCID 895258586-Chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 118271714HCID 118271714, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 92000389Chloropalladium(1+) 2-(2-aminoethyl)benzen-1-ide--di-tert-butyl[2',4',6'-tri(propan-2-yl)[1,1'-biphenyl]-2-yl]phosphane (1/1/1)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridine (0.5 g, 0.96 mmol) in anhydrous THF (5 mL) was added 1,1,1-trifluoropropan-2-amine (0.13 g, 1.2 mmol), t-Bu-X-Phos precatalyst (0.1 g, 0.14 mmol) and sodium-t-Butoxide (0.27 g, 2.8 mmol). The contents were heated to 80° C. in a sealed reaction vessel under inert atmosphere. After 4 h, the reaction mixture was brought back to ambient temperature, the reaction was quenched with H2O (10 mL) and the organic contents were extracted with EtOAc (2×50 mL), dried over Na2SO4 and concentrated. The residue thus obtained was purified by flash column chromatography, to afford the title compound (0.32 g, 67% yield). MS ESI calc'd. for C28H22ClF3N4 [M+H]+ 507. Found 507.

Workup

  1. customwas brought back to ambient temperature
  2. customthe reaction was quenched with H2O (10 mL)
  3. extractionthe organic contents were extracted with EtOAc (2×50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue thus obtained
  7. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-cd0222059da44893a9c04f9775b12627
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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