Cesium carbonate → HCID 86724450, compound

HRID 2369556Notes

Reaction equation

HRID 2369556 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[C:15]3[C:10](=[C:11]([CH3:16])[N:12]=[CH:13][CH:14]=3)[CH2:9][O:8][C:6]=2[CH:7]=1.[C:17]([O:21][C:22]([NH:24][CH:25]([CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:26][OH:27])=[O:23])([CH3:20])([CH3:19])[CH3:18].C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.CCOC(C)=O.O.CC([O-])=O.CC([O-])=O.[Pd+2].C(P(C(C)(C)C)C1C=CC=CC=1C1C(CCC)=CC(CCC)=CC=1CCC)(C)(C)C>[C:17]([O:21][C:22](=[O:23])[NH:24][C@@H:25]([CH2:28][CH:29]([CH3:30])[CH3:31])[CH2:26][O:27][C:2]1[CH:3]=[CH:4][C:5]2[C:15]3[C:10](=[C:11]([CH3:16])[N:12]=[CH:13][CH:14]=3)[CH2:9][O:8][C:6]=2[CH:7]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

9

Reactant 3

HCID 10796Cesium carbonateHCID 546110tert-butyl N-(1-hydroxy-4-methylpentan-2-yl)carbamateHCID 86695952HCID 86695952, compound

Product 1

HCID 86724450HCID 86724450, compoundYield 187.3%

Reagents, catalysts & solvents 5

HCID 167845palladium(II) acetateCatalystHCID 67346612HCID 67346612, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 8-chloro-4-methyl-5H-chromeno[3,4-c]pyridine (60 mg, 0.259 mmol), (S)-(+2-(tert-butoxycarbonylamino)-4-methyl-1-pentanol (113 mg, 0.518 mmol), 2-di-t-butylphosphino-2′,4′,6′-tri-1-propyl-1,1′-biphenyl (6.60 mg, 0.016 mmol), Cs2CO3 (127 mg, 0.388 mmol) and Pd(OAc)2 (1.744 mg, 7.77 μmol) in toluene (5 mL) was heated at 80° C. for 16 h. After cooling to rt, the mixture was diluted with EtOAc (10 mL) and water (10 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to afford (S)-tert-butyl(4-methyl-1-((4-methyl-5H-chromeno[3,4-c]pyridin-8-yl)oxy)pentan-2-yl)carbamate, (0.2 g, 0.485 mmol, 30% yield) as a yellow solid. LCMS (ESI) m/e 413.39 [(M+H)+, calcd for C24H33N2O4 413.24]; LC/MS retention time (Method F): tR=0.97 min.

Workup

  1. dry with materialThe organic layer was dried over Na2SO4
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-64d91d02c03e4d709cb89f6dc875dbe2
Source dataset
uspto-grants-2014_04
Patent number
US08703953B2

Reaction notes

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