Trifluoroacetic acid → HCID 45096601, compound

HRID 859150Notes

Reaction equation

HRID 859150 reaction equation
[C:1]([C:4]1[C:5]([CH3:13])=[N:6][N:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=12)([CH3:3])=[CH2:2].C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]([C:4]1[C:5]([CH3:13])=[N:6][N:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=12)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 69588575HCID 69588575, compound

Product 1

HCID 45096601HCID 45096601, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-isopropenyl-2-methylpyrazolo[1,5-a]pyridine (0.43 g, 2.5 mmol) in CH2Cl2 (30 mL) was treated with triethylsilane (3 mL, 18.8 mmol) and TFA (6 mL). The reaction was stirred at room temperature for 15 hours then quenched with saturated NaHCO3.The layers were separated and the aqueous layer was extracted with CH2Cl2 and the combined organic layers was dried over MgSO4 and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to column chromatography (20% ethyl acetate/heptane) to give 0.19 g (44%) of a yellow oil as the title compound: 1H NMR (400 MHz, DMSO-d6) δ 8.45 (d, J=7.0 Hz, 1H), 7.59 (d, J=8.9 Hz, 1H), 7.07–7.03 (m, 1H), 6.71–6.68 (m, 1H), 3.20–3.09 (m, 1H), 2.35 (s, 3H), 1.31 (d, J=7.1 Hz, 6H); 13CNMR (100 MHz, DMSO-d6)δ 147.5, 137.1, 128.1, 121.9, 116.6, 113.5, 110.2, 23.8, 22.7, 12.4; HRMS (FAB) calcd for C11H14N2+H 175.1235. found 175.1236.

Workup

  1. customthen quenched with saturated NaHCO3
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. dry with materialthe combined organic layers was dried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-3cea780a80244a3bbe4995ea8654af6a
Source dataset
uspto-grants-2006_12
Patent number
US07151109B2

Reaction notes

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