Triphenylphosphine → HCID 15293176, compound

HRID 128945Notes

Reaction equation

HRID 128945 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[N:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:11](=[O:18])[NH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[CH2:24]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>>[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[CH2:24][N:10]1[CH:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[C:17]2[N:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:11]1=[O:18]

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 694672-ThiophenemethanolHCID 5363146Diisopropyl azodicarboxylateHCID 19373031HCID 19373031, compound

Product 1

HCID 15293176HCID 15293176, compoundYield 56%

Procedure

To a suspension of 8-(3-chlorophenyl)-1,6-naphthyridin-5-one (128 mg, 0.5 mmoles), thiophenemethanol (0.08 ml, 0.6 mmoles), and triphenylphosphine (197 mg, 0.75 mmoles) was added dropwise diisopropylazodicarboxylate (0.15 ml, 0.75 mmoles) under an atmosphere of nitrogen at 21° C. The reaction mixture was stirred overnight and concentrated under vacuum to give an oil. The oil was chromatographed with silica gel (eluting with 1:4 ethyl acetate/hexane) to give (after crystallization from methanol) 98 mg (56% yield) of the desired 6-(2-thienylmethyl)-8-(3-chlorophenyl)-1,6-naphthyridin-5-one as a white solid: mp 141.5°-145.0° C; 1H NMR (CDCl3, 300 MHz) δ5.41 (s, 2H), 6.97-7.56 (m, 9H), 8.78 (dd, 1H, J=8.1, 1.9), 8.93 (dd, 1H, J=4.5, 1.9); 13C NMR (75 MHz, CDCl3) δ161.56, 154.34, 151.68, 137.91, 136.93, 136.79, 134.14, 133.70, 130.04, 129.54, 128.26, 127.81, 127.77, 127.09, 126.65, 122.13, 121.91, 120.05, 46.85; IR (KBr) vmax 1643, 1612, 1591, 1564, 1552, 1483, 1441, 1429, 1415, 1377, 1358, 1302, 1207, 1174, 792, 763, 734, 715, 696, 601 cm-1 ; mass spectrum (EI), m/e 352. Anal. (C19H13ClN2OS) Calcd.: C, 64.68; H, 3.71; N, 7.94. Found: C, 64.45; H, 3.69; N, 8.00.

Workup

  1. concentrationconcentrated under vacuum
  2. customto give an oil
  3. customThe oil was chromatographed with silica gel (eluting with 1:4 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0a4adfe7d58547a99430c90481707d32
Source dataset
uspto-grants-1995_11
Patent number
US05466697

Reaction notes

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