Diisopropylethylamine → HCID 86696264, compound
Reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][C:11]([NH:17][CH2:18][CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])=[CH:10]2)(=O)=O.[CH3:30][N:31]1[CH:35]=[C:34]([C:36]2[CH:37]=[CH:38][C:39]3[N:40]([C:42]([SH:45])=[N:43][N:44]=3)[CH:41]=2)[CH:33]=[N:32]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.CCN(C(C)C)C(C)C>CN(C=O)C.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]>[Si:21]([O:20][CH2:19][CH2:18][NH:17][C:11]1[CH:12]=[N:13][C:14]2[C:9]([CH:10]=1)=[CH:8][C:7]([S:45][C:42]1[N:40]3[CH:41]=[C:36]([C:34]4[CH:33]=[N:32][N:31]([CH3:30])[CH:35]=4)[CH:37]=[CH:38][C:39]3=[N:44][N:43]=1)=[CH:16][CH:15]=2)([C:24]([CH3:25])([CH3:26])[CH3:27])([CH3:22])[CH3:23]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 110 °C
Procedure
A mixture of Intermediate Q28 (0.2 g, 0.444 mmol), Intermediate E (0.103 g, 0.444 mmol), xantphos (0.051 g, 0.089 mmol), Pd2(dba)3 (0.041 g, 0.044 mmol) and DIPEA (0.155 ml, 0.888 mmol) in DMF (10 ml) was bubbled with Ar gas for 10 min and then the reaction mixture was stirred under MW radiation at 110° C. for 1 h. The solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (DCM/MeOH=40/1) to afford the title compound as brown oil (0.1 g, 42.4% yield). LCMS (method B): [M+H]+=532, tR=2.74 min.
Workup
- customwas bubbled with Ar gas for 10 min
- customThe solvent was removed under reduced pressure
- customThe residue was purified by silica gel chromatography (DCM/MeOH=40/1)
Sources & evidence
- ORD record
- ord-d18e01fb0c0a45efb19a686db8dca826
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09062045B2
Reaction notes
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