Cesium carbonate → HCID 86726520, compound

HRID 1487692Notes

Reaction equation

HRID 1487692 reaction equation
Cl[C:2]1[N:3]=[C:4]([O:29][CH:30]2[CH2:34][CH2:33][O:32][CH2:31]2)[C:5]2[C:10]([C:11]3[CH:20]=[CH:19][C:14]4[N:15]=[C:16]([CH3:18])[O:17][C:13]=4[CH:12]=3)=[CH:9][N:8]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:6]=2[N:7]=1.[NH2:35][C:36]1[CH:46]=[CH:45][C:39]([C:40]([N:42]([CH3:44])[CH3:43])=[O:41])=[CH:38][C:37]=1[CH3:47].C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:44][N:42]([CH3:43])[C:40](=[O:41])[C:39]1[CH:45]=[CH:46][C:36]([NH:35][C:2]2[N:3]=[C:4]([O:29][CH:30]3[CH2:34][CH2:33][O:32][CH2:31]3)[C:5]3[C:10]([C:11]4[CH:20]=[CH:19][C:14]5[N:15]=[C:16]([CH3:18])[O:17][C:13]=5[CH:12]=4)=[CH:9][N:8]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:27])([CH3:26])[CH3:28])[C:6]=3[N:7]=2)=[C:37]([CH3:47])[CH:38]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 167817704-amino-N,N,3-trimethylbenzamideHCID 86726519HCID 86726519, compound

Product 1

HCID 86726520HCID 86726520, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a suspension of 6-(2-chloro-4-((tetrahydrofuran-3-yl)oxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbenzo[d]oxazole (1 equiv) in 1,4-dioxane (0.24 M) was added 4-amino-N,N,3-trimethylbenzamide (1 equiv), cesium carbonate (3 equiv), palladium acetate (0.3 equiv) and 2,2′-bis-diphenylphosphanyl-[1,1′]binaphthalene (0.6 equiv). The resulting reaction mixture was refluxed at 110° C. for 3 h. The reaction mixture was filtered and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (5% MeOH in DCM) to afford the title compound (72% yield). MS (ESI) m/z 643.1 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by silica gel chromatography (5% MeOH in DCM)

Sources & evidence

ORD record
ord-3545addff7164339a58fb958e672a970
Source dataset
uspto-grants-2016_08
Patent number
US09428509B2

Reaction notes

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