N,N,N',N'-Tetramethylazodicarboxamide → HCID 22614920, compound

HRID 843138Notes

Reaction equation

HRID 843138 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([O:11][CH:12]3[CH2:17][CH2:16][N:15]([CH2:18][C:19]4[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=4)[CH2:14][CH2:13]3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH2:25][OH:26].[CH2:27]([O:29][CH2:30][C:31]1[O:32][C:33]2[CH:39]=[CH:38][C:37](O)=[CH:36][C:34]=2[CH:35]=1)[CH3:28].N(C(N(C)C)=O)=NC(N(C)C)=O.C(P(CCCC)CCCC)CCC>C1COCC1.C(OCC)(=O)C>[CH2:27]([O:29][CH2:30][C:31]1[O:32][C:33]2[CH:39]=[CH:38][C:37]([O:26][CH2:25][C:3]3[O:4][C:5]4[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH:12]5[CH2:17][CH2:16][N:15]([CH2:18][C:19]6[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=6)[CH2:14][CH2:13]5)[C:6]=4[C:2]=3[CH3:1])=[CH:36][C:34]=2[CH:35]=1)[CH3:28]

Participants

7

Reactant 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 22615057HCID 22615057, compoundHCID 22615112HCID 22615112, compound

Product 1

HCID 22614920HCID 22614920, compoundYield 61.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-30 °C

Procedure

To a cooled (−30° C.) solution of [3-methyl-4-(1-pyridin-3-ylmethyl-piperidin-4-yloxy)-benzofuran-2-yl]-methanol (30 mg), 2-ethoxymethyl-benzofuran-5-ol (16 mg) and 1,1′-azobis(N,N-dimethylformamide) (37 mg) in THF (1 ml) was added tributylphosphine (53 μl) and the resulting solution was stirred overnight at −30° C. The resulting suspension was diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by preparative thin layer chromatography (using dichloromethane:MeOH=20:1 as a developing solvent) to give 3-[4-[2-(2-ethoxymethyl-benzofuran-5-yloxymethyl)-3-methyl-benzofuran-4-yloxy]-piperidin-1-ylmethyl]-pyridine (27 mg) as a colorless oil. FAB-MS: m/z 527 (MH+); 1H-NMR (CDCl3): δ 1.26 (3H, t, J=7 Hz), 1.99 (4H, m), 2.41 (3H, s), 2.42 (2H, m), 2.70 (2H, m), 3.55 (2H, s), 3.61(2H, q, J=7 Hz), 4.52 (1H, m), 4.58 (2H, s), 5.10 (2H, s), 6.60 (1H, d, J=8 Hz), 6.63 (1H, s), 6.97 (1H, dd, J1=9 Hz, J2=2.5 Hz), 7.03 (1H, d, J=8 Hz), 7.15 (1H, t, J=8 Hz), 7.15 (1H, d, J=2.5 Hz), 7.26 (1H, dd, J1=8 Hz, J2=5 Hz), 7.37 (1H, d, J=9 Hz), 7.68 (1H, dt, J1=8 Hz, J2=2 Hz),8.51 (1H, dd, J1=5 Hz, J2=2 Hz), 8.56 (1H, d, J=2 Hz).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated to dryness
  4. customThe residue was purified by preparative thin layer chromatography (

Sources & evidence

ORD record
ord-183f2ef578ba49ca9d095711b868fc8f
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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