HCID 22612166, compound → HCID 22612121, compound

HRID 844063Notes

Reaction equation

HRID 844063 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:24]=[CH:25][CH:26]=1)[O:7][C:8]1[N:23]=[CH:22][CH:21]=[CH:20][C:9]=1[C:10]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1)=[O:11])(=[O:3])[CH3:2].C[Li].[CH2:29]1COCC1.C1(C(C)C)C=CC=CC=1>O1CCCC1>[OH:3][C:1]([C:4]1[CH:5]=[C:6]([CH:24]=[CH:25][CH:26]=1)[O:7][C:8]1[N:23]=[CH:22][CH:21]=[CH:20][C:9]=1[C:10]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1)=[O:11])([CH3:29])[CH3:2]

Participants

5

Reactant 3

HCID 22612166HCID 22612166, compoundHCID 70153969HCID 70153969, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 22612121HCID 22612121, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-(3-Acetyl-phenoxy)-N-pyridin-4-ylmethyl-nicotinamide (0.180 grams, 0.51 mmole) in tetrahydrofuran (20 ml) at −78° C. 1.0 M methyl lithium in THF/cumene (1.14 ml, 1.14 mmole) was added and stirred at −78° C. for 1 hour. The reaction was quenched with water and diluted with ethyl acetate. The organics were washed with water and brine, dried over MgSO4, filtered and concentrated to give a product which was purified by chromatography on silica eluting with ethyl acetate to give a white foam. MS (m/e) 364 (M++1); 1H NMR (CDCl3) d 1.58 (6H, s), 4.70 (2H, d, J=5.81 Hz), 7.0-8.7 (12H, m).

Workup

  1. customat −78° C
  2. customThe reaction was quenched with water
  3. additiondiluted with ethyl acetate
  4. washThe organics were washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a product which
  9. customwas purified by chromatography on silica eluting with ethyl acetate
  10. customto give a white foam

Sources & evidence

ORD record
ord-5efebb122eac4bc2b45a4b491095f135
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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