Cesium carbonate → HCID 86726474, compound

HRID 1487638Notes

Reaction equation

HRID 1487638 reaction equation
Cl[C:2]1[N:3]=[C:4]([O:38][CH:39]([CH3:41])[CH3:40])[C:5]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([C:17]4[N:18]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[CH:19]=[CH:20][N:21]=4)=[CH:13][CH:12]=3)=[CH:9][N:8]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:6]=2[N:7]=1.[NH2:42][C:43]1[CH:51]=[CH:50][C:46]([C:47]([NH2:49])=[O:48])=[CH:45][C:44]=1[O:52][CH3:53].[C:54](=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>[CH:39]([O:38][C:4]1[C:5]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([C:17]4[N:18]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[CH:19]=[CH:20][N:21]=4)=[CH:13][CH:12]=3)=[CH:9][N:8]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:6]=2[N:7]=[C:2]([NH:42][C:43]2[CH:51]=[CH:50][C:46]([C:47]([NH:49][CH3:54])=[O:48])=[CH:45][C:44]=2[O:52][CH3:53])[N:3]=1)([CH3:41])[CH3:40]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 539237984-Amino-3-methoxybenzamideHCID 86726465HCID 86726465, compound

Product 1

HCID 86726474HCID 86726474, compoundYield 60%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

To a degassed mixture of 2-chloro-4-isopropoxy-7-((2-(trimethylsilyl)ethoxy)methyl)-5-(4-(1-((2-(trimethylsilyl)-ethoxy)methyl)-1H-imidazol-2-yl)phenyl)-7H-pyrrolo[2,3-d]pyrimidine (1 equiv), 4-amino-3-methoxybenzamide (1.2 equiv) and cesium carbonate (3.0 equiv) in 1,4-dioxane (0.07 M) was added palladium acetate (0.1 equiv) and 2,2′-bis-diphenylphosphanyl-[1,1′]binaphthalenyl (0.3 equiv). The reaction was stirred at 100° C. for 3 h. After the reaction was complete, the reaction mixture was cooled to room temperature and concentrated. The residue was purified by silica gel chromatography (0-2% DCM in MeOH) to afford the crude title compound (60% yield) as a yellow solid. MS (ESI) m/z 758.2 [M+1]+.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel chromatography (0-2% DCM in MeOH)

Sources & evidence

ORD record
ord-1275aa09ab8b4509a64ffec4394a7f09
Source dataset
uspto-grants-2016_08
Patent number
US09428509B2

Reaction notes

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