Cesium carbonate → Tert-butyl[4'-(3,4-dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-6'-yl]-methyl-carbamate

HRID 469370Notes

Reaction equation

HRID 469370 reaction equation
[CH3:1][NH:2][C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].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.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:59]1[N:64]=[C:63]([N:65]2[CH2:70][CH2:69][CH:68]([N:71]3[C:79]4[C:74](=[N:75][CH:76]=[CH:77][CH:78]=4)[NH:73][C:72]3=[O:80])[CH2:67][CH2:66]2)[CH:62]=[C:61]([C:81]([C:83]2[CH:93]=[C:92]([CH3:94])[C:86]3[N:87]([CH3:91])[C:88](=[O:90])[O:89][C:85]=3[CH:84]=2)=[O:82])[CH:60]=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:5]([O:4][C:3](=[O:9])[N:2]([C:59]1[N:64]=[C:63]([N:65]2[CH2:70][CH2:69][CH:68]([N:71]3[C:79]4[C:74](=[N:75][CH:76]=[CH:77][CH:78]=4)[NH:73][C:72]3=[O:80])[CH2:67][CH2:66]2)[CH:62]=[C:61]([C:81]([C:83]2[CH:93]=[C:92]([CH3:94])[C:86]3[N:87]([CH3:91])[C:88](=[O:90])[O:89][C:85]=3[CH:84]=2)=[O:82])[CH:60]=1)[CH3:1])([CH3:8])([CH3:7])[CH3:6]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 527635tert-Butyl methylcarbamateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 252701311-[6'-chloro-4'-(3,4-dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

Product 1

HCID 58181138Tert-butyl[4'-(3,4-dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-6'-yl]-methyl-carbamate

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Under an argon atmosphere 13 mg (0.96 mmol) tert-butyl methyl-carbamate, 11 mg (0.019 mmol) Xantphos, 8.8 mg (0.010 mmol) Pd2 dba3 and 47 mg (0.15 mmol) caesium carbonate were added to 50 mg (0.10 mmol) 1-[6′-chloro-4′-(3,4-dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-1,3-dihydro-imidazo[4,5-b]pyridin-2-one in 1.00 mL dioxane and the mixture was refluxed for 15 h with stirring. The reaction mixture was evaporated down i. vac. and the residue obtained was used in the next step without further purification.

Workup

  1. temperaturethe mixture was refluxed for 15 h
  2. customThe reaction mixture was evaporated down i
  3. customand the residue obtained
  4. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-585d798c702f4daa9deaff75af64417b
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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