Water → HCID 54282996, compound

HRID 1742430Notes

Reaction equation

[CH2:1]([C:5]1[N:13]([C:14]2[C:23]3[C:18](=[CH:19][C:20]([Sn](CCCC)(CCCC)CCCC)=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4].I[C:38]1[CH:47]=[CH:46][CH:45]=[CH:44][C:39]=1[C:40]([O:42][CH3:43])=[O:41].O>CN(C=O)C>[CH3:43][O:42][C:40](=[O:41])[C:39]1[CH:44]=[CH:45][CH:46]=[CH:47][C:38]=1[C:20]1[CH:21]=[CH:22][C:23]2[C:18](=[CH:17][CH:16]=[CH:15][C:14]=2[N:13]2[C:8]3=[N:9][CH:10]=[CH:11][CH:12]=[C:7]3[N:6]=[C:5]2[CH2:1][CH2:2][CH2:3][CH3:4])[CH:19]=1

Participants

Conditions

Temperature: 105 °C

Procedure

A mixture of 2-butyl-3-(6-tributylstannanyl-naphthalen-1-yl)-3H-imidazo[4,5-b]-pyridine (120 mg, 0.22 mmol), methyl 2-iodobenzoate (79 mg, 0.3 mmol) and PdCl2 (PPh3)2 (15 mg, 0.02 mmol) in 1.0 mL DMF was heated at 105° C. for 20 hours. The cooled reaction mixture was poured into H2O (20 mL). The aqueous solution was extracted with EtOAc (3×50 mL). The combined extracts were washed with saturated aqueous NaHCO3 (25 mL), dried MgSO4) and concentrated in vacuo. The residue was chromatographed on SiO2 -gel using a gradient of 20% ethyl acetate/hexanes to 100% ethyl acetate to give 40 mg of product. 1H NMR (250 MHz, CDCl3): d 8.27 (dd, 1H, J=1.15, 4.85 Hz), 8.14 (dd, 1H, J=1.21, 7.96 Hz), 8.08 (d, 1H, J=8.2 Hz), 7.94 (d, 1H, J=1.4 Hz), 7.89 (d, 1H, J=7.9 Hz), 7.69 (t, 1 H), 7.58 (m), 7.48 (m), 7.26 (m), 7.14 (d, 1H, J=8.5 Hz), 3.57 (s, 3 H), 2.72 (t, 2 H), 1.78 (m, 2 H), 1.27 (m, 2 H), 0.83 (t, 3 H).

Workup

customThe cooled reaction mixture
extractionThe aqueous solution was extracted with EtOAc (3×50 mL)
washThe combined extracts were washed with saturated aqueous NaHCO3 (25 mL), dried MgSO4) and
concentrationconcentrated in vacuo
customThe residue was chromatographed on SiO2

Sources & evidence

ORD record: ord-42e96fa1d14340e89606c881c6d64084
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05338740

Reaction notes

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