Cesium carbonate → Benzyl 4-(2-chloropyridin-4-yl)-3-oxo-2,4-diazabicyclo[3.1.0]hexane-2-carboxylate
Reaction equation
[O:1]=[C:2]1[NH:7][CH:6]2[CH:4]([CH2:5]2)[N:3]1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].[Cl:18][C:19]1[CH:24]=[C:23](I)[CH:22]=[CH:21][N:20]=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.C(=O)([O-])[O-].[Cs+].[Cs+]>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].O1CCOCC1>[Cl:18][C:19]1[CH:24]=[C:23]([N:7]2[CH:6]3[CH:4]([CH2:5]3)[N:3]([C:8]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:9])[C:2]2=[O:1])[CH:22]=[CH:21][N:20]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Using analogous reagents and reaction conditions as described in Example 1 above, benzyl 3-oxo-2,4-diazabicyclo[3.1.0]hexane-2-carboxylate (200 mg, 0.861 mmol) was reacted with 2-chloro-4-iodopyridine (227 mg, 0.947 mmol), xantphos (45 mg, 0.077 mmol), Pd2(dba)3 (24 mg, 0.025 mmol), cesium carbonate (421 mg, 1.29 mmol) and 1,4-dioxane (12 mL) at 100° C. for 3 hours. Purification by column chromatography on silica gel (50% ethyl acetate in hexane) afforded 220 mg of the product (75% yield).
Workup
- customreagents and reaction conditions
- customPurification by column chromatography on silica gel (50% ethyl acetate in hexane)
Sources & evidence
- ORD record
- ord-d3f7667311524b91a37914c6abff7aba
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09029399B2
Reaction notes
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