Sodium Carbonate → HCID 178455340, compound

HRID 2235240Notes

Reaction equation

HRID 2235240 reaction equation
[C:1]([Si:5]([CH3:37])([CH3:36])[O:6][C@@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]2[CH2:17][CH2:16][CH:15]([CH2:18][C:19]3[C:24]([Cl:25])=[CH:23][C:22](OS(C(F)(F)F)(=O)=O)=[CH:21][C:20]=3[Cl:34])[C:14]2=[O:35])[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[N:38]1[CH:43]=[CH:42][CH:41]=[C:40](B(O)O)[CH:39]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(COC)OC>[C:1]([Si:5]([CH3:36])([CH3:37])[O:6][C@@H:7]1[CH2:8][CH2:9][C@H:10]([N:13]2[CH2:17][CH2:16][CH:15]([CH2:18][C:19]3[C:20]([Cl:34])=[CH:21][C:22]([C:40]4[CH:39]=[N:38][CH:43]=[CH:42][CH:41]=4)=[CH:23][C:24]=3[Cl:25])[C:14]2=[O:35])[CH2:11][CH2:12]1)([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 178455344HCID 178455344, compound

Product 1

HCID 178455340HCID 178455340, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Using the method of Example 81 and trifluoro-methanesulfonic acid 4-{1-[cis-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-2-oxo-pyrrolidin-3-yl methyl}-3,5-dichloro-phenyl ester (Preparation 74) (0.204 g, 0.337 mmol), 3-pyridineboronic acid (0.124 g, 1.01 mmol), tetrakis(triphenylphosphine)palladium (0.039 g, 0.0337 mmol), dimethoxyethane (5 mL) and sodium carbonate (2M, 0.9 mL) gives the title compound. Purify the crude material over silica gel (3/1 hexane in ethyl acetate to ethyl acetate) to yield 0.027 g (15%) of the title compound: mass spectrum (m/z): 535(M+1).

Sources & evidence

ORD record
ord-9d4f0b90aa044eb4ba57628901cae620
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

Loading…