Morpholine → HCID 86696258, compound
Reaction equation
C([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][C:9](Br)=[CH:8]2)(=O)C.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CC([O-])(C)C.[K+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N:16]1([C:9]2[CH:10]=[N:11][C:12]3[C:7]([CH:8]=2)=[CH:6][C:5]([OH:4])=[CH:14][CH:13]=3)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
A mixture of Intermediate A (0.8 g, 3.01 mmol), morpholine (1.048 g, 12.03 mmol), Pd2(dba)3 (0.275 g, 0.301 mmol), xantphos (0.305 g, 0.602 mmol) and KOtBu (0.337 g, 3.01 mmol) in toluene (15 ml) was bubbled with N2 for 15 min and then was heated at 100° C. for 5 h under MW radiation. The mixture was quenched with saturated aqueous NaHCO3 solution. The aqueous phase was extracted with DCM/IPA (10 ml, v/v=3/1) for 3 times. The combined extract was dried over anhydrous MgSO4. Filtered and concentrated, the residue was purified by silica gel chromatography to afford the title compound (0.31 g, 40.3% yield). LCMS (method B): [M+H]+=231, tR=1.1 min.
Workup
- customwas bubbled with N2 for 15 min
- customThe mixture was quenched with saturated aqueous NaHCO3 solution
- extractionThe aqueous phase was extracted with DCM/IPA (10 ml, v/v=3/1) for 3 times
- extractionThe combined extract
- dry with materialwas dried over anhydrous MgSO4
- filtrationFiltered
- concentrationconcentrated
- customthe residue was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-91076422a1b44f498da70fdd12d9b1af
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09062045B2
Reaction notes
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