Triethylamine → HCID 69591888, compound
Reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[C:23]([N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)(=[O:26])[CH:24]=[CH2:25].C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O.CC([O-])=O.CC([O-])=O.[Pd+2].O>[N:27]1([C:23](=[O:26])[CH:24]=[CH:25][C:2]2[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][CH:17]4[CH2:22][CH2:21][CH2:20][CH2:19][O:18]4)=[CH:12][CH:11]=3)=[CH:4][CH:3]=2)[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1Participants
Conditions
- Temperature
- 90 °C
Procedure
To a solution of (4-iodo-phenyl)-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-amine (0.265 g, 0.65 mmol) in 2 mL dimethylformamide was added 4-acryloylmorpholine (0.110 g, 0.78 mmol), Pd(OAc)2 (0.029 g, 0.13 mmol), and triethylamine (0.20 mL, 1.43 mmol). The reaction was stirred at 90° C. for 2 hr. Triphenylphosphine (0.101 g, 0.38 mmol) and additional Pd(OAc)2 (0.032 g, 0.14 mmol) were added and the reaction mixture was stirred at 90–100° C. for 18 hr. The reaction mixture was cooled, water was added, and the aqueous solution was washed ethyl acetate (3×). The combined organic layers were dried (magnesium sulfate) and concentrated. Medium pressure silica gel chromatography (33% ethyl acetate/hexanes to 50% ethyl acetate/hexanes) afforded the title compound of Step A. MS 423.0 (M+1)+
Workup
- stirringthe reaction mixture was stirred at 90–100° C. for 18 hr
- temperatureThe reaction mixture was cooled
- washthe aqueous solution was washed ethyl acetate (3×)
- dry with materialThe combined organic layers were dried (magnesium sulfate)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-829896c40fae42c2899c24dff3e2714c
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07053212B2
Reaction notes
Loading…