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Cesium carbonate → HCID 86724450, compound

HRID 870964
Notes
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Reaction equation

HRID 870964 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][C@@H: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>[CH3:30][CH:29]([CH3:31])[CH2:28][C@H:25]([NH:24][C:22](=[O:23])[O:21][C:17]([CH3:20])([CH3:19])[CH3:18])[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 3

HCID 10796Cesium carbonateHCID 7018766Boc-L-leucinolHCID 86695952HCID 86695952, compound

Product 1

HCID 86724450HCID 86724450, compoundYield 187.3%

Reagents, catalysts & solvents 5

HCID 167845palladium(II) acetateCatalyst
HCID 67346612
HCID 67346612, compound
Catalyst
HCID 962WaterSolvent
HCID 1140TolueneSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

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. temperatureAfter cooling to rt
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fad848ec65774a1d864e35636cb27a1e
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08969564B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes