Triethylsilane → HCID 67071808, compound

HRID 1260549Notes

Reaction equation

HRID 1260549 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:11]=[N:12][C:13]([O:16][CH:17]([CH3:19])[CH3:18])=[CH:14][CH:15]=2)=O)=[CH:4][CH:3]=1.C([SiH](CC)CC)C>C1COCC1>[CH:17]([O:16][C:13]1[N:12]=[CH:11][C:10]([CH2:8][C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=2)=[CH:15][CH:14]=1)([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 12052Triethylsilane2×HCID 67071756HCID 67071756, compound

Product 1

HCID 67071808HCID 67071808, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(4-Hydroxyphenyl)-(6-isopropoxypyridin-3-yl)methanone (300 mg, 1.17 mmol) was dissolved in 15 ml of THF. Following addition of triethylsilane (678 mg, 5.83 mmol) the mixture was stirred at room temperature for 2 days. Following addition of 116 mg of triethylsilane the mixture was stirred at 60° C. for 8 h, concentrated and admixed with ethyl acetate and water, and the organic phase was separated off, concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 52 mg (18%), M+H+: 244.14.

Workup

  1. stirringwas stirred at 60° C. for 8 h
  2. concentrationconcentrated
  3. customthe organic phase was separated off
  4. concentrationconcentrated
  5. custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-3c1abb66b82a41b69e34571a464cf7fa
Source dataset
uspto-grants-2013_06
Patent number
US08470841B2

Reaction notes

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