Acetamide → HCID 89827691, compound

HRID 715103Notes

Reaction equation

HRID 715103 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:13]3[C:14]([F:28])=[CH:15][C:16]([F:27])=[C:17]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:18]=3)[C:8]([CH3:12])=[N:9]2)=[CH:4][N:3]=1.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+].[C:77]([NH2:80])(=[O:79])[CH3:78]>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:77]([NH:80][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:13]3[C:14]([F:28])=[CH:15][C:16]([F:27])=[C:17]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:23])[CH3:24])[CH:18]=3)[C:8]([CH3:12])=[N:9]2)=[CH:4][N:3]=1)(=[O:79])[CH3:78]

Participants

7

Reactant 4

HCID 178AcetamideHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 89827736HCID 89827736, compound

Product 1

HCID 89827691HCID 89827691, compoundYield 90%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

Sparge a mixture of tert-butyl (5-(7-chloro-2-methyl-1,6-naphthyridin-3-yl)-2,4-difluorophenyl)carbamate (0.664 g, 1.636 mmol), XantPhos (0.189 g, 0.327 mmol), Cs2CO3 (1.066 g, 3.27 mmol) and acetamide (0.483 g, 8.18 mmol) in dioxane (16 mL) with Ar, add Pd2(dba)3 (0.150 g, 0.164 mmol) and heat at 100° C. overnight. Cool to RT, remove the solids via filtration through diatomaceous earth, rinse well with THF, concentrate the filtrate to dryness and purify via silica gel chromatography (EtOAc/Hex) to afford the title compound (630 mg, 90%) as a glass. MS (ESI) m/z: 429.2 (M+H+).

Workup

  1. customSparge
  2. temperatureCool to RT
  3. customremove the solids
  4. filtrationvia filtration through diatomaceous earth
  5. washrinse well with THF
  6. concentrationconcentrate the filtrate to dryness
  7. custompurify via silica gel chromatography (EtOAc/Hex)

Sources & evidence

ORD record
ord-8c6720f76bea4b02bdb75b9c34e9e307
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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