Isopropanol → 4-[4-(4-Thiophen-3-yl-phenoxy)-phenyl]-morpholine

HRID 2353261Notes

Reaction equation

HRID 2353261 reaction equation
I[C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[S:21]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22]1.C(=O)([O-])[O-].[K+].[K+].CC(O)C>[Pd].O>[S:21]1[CH:25]=[CH:24][C:23]([C:2]2[CH:20]=[CH:19][C:5]([O:6][C:7]3[CH:12]=[CH:11][C:10]([N:13]4[CH2:18][CH2:17][O:16][CH2:15][CH2:14]4)=[CH:9][CH:8]=3)=[CH:4][CH:3]=2)=[CH:22]1

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 11430Potassium CarbonateHCID 581760Thiophene-3-boronic acidHCID 236277884-[4-(4-Iodo-phenoxy)-phenyl]-morpholine

Product 1

HCID 236277894-[4-(4-Thiophen-3-yl-phenoxy)-phenyl]-morpholineYield 35.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

The title compound (25 mg, 35%) was prepared by treating 4-[4-(4-Iodo-phenoxy)-phenyl]-morpholine (80 mg, 0.21 mmol) from Example 24 with thiophene-3-boronic acid (35 mg, 0.25 mmol) in the presence of 10% Pd/C (10 mg), potassium carbonate (87 mg, 0.68 mmol), 2-propanol (4 mL) and water (0.4 mL) by using the procedure described in step 2 of Example 16: MS (ESI) m/z 338 (M+H); 1H NMR (400 MHz, CDCl3) δ 3.13 (t, J=4.8 Hz, 4H), 3.87 (t, J=4.8 Hz, 4H), 6.91-7.01 (m, 6H), 7.34-7.38 (m, 3H), 7.51-7.53 (m, 2H).

Sources & evidence

ORD record
ord-1632a45d712b4f809873e11c2d1ef081
Source dataset
uspto-grants-2010_07
Patent number
US07750012B2

Reaction notes

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