Cesium carbonate → tert-Butyl (1S,3R)-3-(4-(4-fluoro-2-methoxyphenyl)pyridin-2-ylcarbamoyl)cyclopentylcarbamate

HRID 1896312Notes

Reaction equation

HRID 1896312 reaction equation
[C:1]([C@@H:4]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:5]1)(=[O:3])[NH2:2].Cl[C:18]1[CH:23]=[C:22]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[O:31][CH3:32])[CH:21]=[CH:20][N:19]=1.C([O-])([O-])=O.[Cs+].[Cs+].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>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.O1CCOCC1>[F:30][C:27]1[CH:28]=[CH:29][C:24]([C:22]2[CH:23]=[CH:18][N:19]=[C:20]([NH:2][C:1]([C@@H:4]3[CH2:8][CH2:7][C@H:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[CH2:5]3)=[O:3])[CH:21]=2)=[C:25]([O:31][CH3:32])[CH:26]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 584326092-Chloro-4-(4-fluoro-2-methoxyphenyl)pyridineHCID 59028693cis-3-(Boc-amino)cyclopentanecarboxamide

Product 1

HCID 86657559tert-Butyl (1S,3R)-3-(4-(4-fluoro-2-methoxyphenyl)pyridin-2-ylcarbamoyl)cyclopentylcarbamate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl (1S,3R)-3-(4-(4-fluoro-2-methoxyphenyl)pyridin-2-ylcarbamoyl)cyclopentylcarbamate was prepared according to Method B using tert-butyl (1S,3R)-3-carbamoylcyclopentylcarbamate (750 mg, 3.28 mmol), 2-chloro-4-(4-fluoro-2-methoxyphenyl)pyridine (930 mg, 3.94 mmol), Cs2CO3 (1.63 g, 4.92 mmol), xantphos (173 mg, 0.29 mmol), Tetrakis(triphenylphosphine)palladium (0) (150 mg, 0.13 mmol) and 1,4-dioxane (10 ml) brought to reaction at 120° C. for 4 h in a sealed tube.

Workup

  1. custombrought to reaction at 120° C. for 4 h in a sealed tube

Sources & evidence

ORD record
ord-510ec2b2f7154eff9660dce73943f3b0
Source dataset
uspto-grants-2013_08
Patent number
US08518948B2

Reaction notes

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