Cesium carbonate → HCID 86758645, compound

HRID 2298050Notes

Reaction equation

HRID 2298050 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:13])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH3:14][C:15]([O:18][C:19](=[O:26])[NH:20][CH:21]1[CH2:25][CH2:24][NH:23][CH2:22]1)([CH3:17])[CH3:16].C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[Cl:13][C:5]1[CH:4]=[CH:3][C:2]([N:23]2[CH2:24][CH2:25][CH:21]([NH:20][C:19]([O:18][C:15]([CH3:17])([CH3:16])[CH3:14])=[O:26])[CH2:22]2)=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 144749Ethyl 5-bromo-2-chlorobenzoateHCID 634876Binap, (A+-)-HCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamate

Product 1

HCID 86758645HCID 86758645, compoundYield 35.7%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

Prepared as described in Example 5a) using 5-bromo-2-chloro-benzoic acid, ethyl ester (0.50 g), 3-pyrrolidinyl-carbamic acid 1,1-dimethylethyl ester (0.42 g), cesium carbonate (0.86 g), palladium (II) acetate (21 mg) and (R)-BINAP (88 mg) and toluene (3 ml) to afford the subtitle compound as an oil (0.25 g).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-46355b0850bf4d3b9a3568ca2d85fcec
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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