Triphenylphosphine → HCID 54063657, compound

HRID 843140Notes

Reaction equation

HRID 843140 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([O:11][CH2:12][CH:13]3[CH2:18][CH2:17][CH2:16][N:15]([CH2:19][C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[CH2:14]3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH2:26][OH:27].[CH2:28]([O:30][C:31]([C:33]1[O:34][C:35]2[CH:41]=[CH:40][C:39](O)=[CH:38][C:36]=2[CH:37]=1)=[O:32])[CH3:29].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OCC)=O)=O)C>C1COCC1>[CH2:28]([O:30][C:31]([C:33]1[O:34][C:35]2[CH:41]=[CH:40][C:39]([O:27][CH2:26][C:3]3[O:4][C:5]4[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH:13]5[CH2:18][CH2:17][CH2:16][N:15]([CH2:19][C:20]6[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=6)[CH2:14]5)[C:6]=4[C:2]=3[CH3:1])=[CH:38][C:36]=2[CH:37]=1)=[O:32])[CH3:29]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22228632Ethyl 5-hydroxybenzofuran-2-carboxylateHCID 54356540[3-Methyl-4-(1-pyridin-3-ylmethyl-piperidin-3-ylmethoxy)-benzofuran-2-yl]-methanol

Product 1

HCID 54063657HCID 54063657, compoundYield 29.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[3-Methyl-4-(1-pyridin-3-ylmethyl-piperidin-3-ylmethoxy)-benzofuran-2-yl]-methanol (107 mg), 5-hydroxybenzofuran-2-carboxylic acid ethyl ester (60 mg), triphenylphosphine (100 mg) and azodicarboxylic acid diethyl ester (70 μl) were dissolved in THF (7 ml). The solution was stirred overnight at room temperature. A white precipitate separated out. The precipitate was filtered out and the filtrate was evaporated to dryness. The residue was separated by silica gel column chromatography developed by dichloromethane-methanol to give 5-[3-methyl-4-(1-pyridin-3-ylmethyl-piperidin-3-ylmethoxy)-benzofuran-2-ylmethoxy]-benzofuran-2-carboxylic acid ethyl ester (48 mg) as a colorless oil. FAB-MS: m/z 555 (MH+); 1H-NMR (CDCl3): δ 1.25-2.23 (7H, m), 1.43 (3H, t, J=7 Hz), 2.24 (3H, s), 2.78 (1H, m), 2.95 (1H, m), 3.47 (1H, d, J=13 Hz), 3.57 (1H, d, J=13 Hz), 3.89 (2H, m), 4.44 (2H, q, J=7 Hz), 5.10 (2H, s), 6.55 (1H, d, J=8 Hz), 7.04 (1H, d, J=8 Hz), 7.14 (1H, dd, J1=9 Hz, J2=2 Hz), 7.23 (3H, m), 7.47 (1H, m), 7.48 (1H, s), 7.66 (1H, br d, J=7 Hz), 8.48 (1H, br d, J=5 Hz), 8.53 (1H, br s).

Workup

  1. customA white precipitate separated out
  2. filtrationThe precipitate was filtered out
  3. customthe filtrate was evaporated to dryness
  4. customThe residue was separated by silica gel column chromatography

Sources & evidence

ORD record
ord-f785f2041a364ae988fe6080d199f080
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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