Cesium carbonate → HCID 178428287, compound

HRID 2070920Notes

Reaction equation

HRID 2070920 reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[N:14]3[N:15]=[C:16]([NH:18][C:19]4[CH:27]=[C:26]5[C:22]([C:23](=O)[C:24](=[O:29])[N:25]5[CH3:28])=[C:21]([CH3:31])[CH:20]=4)[N:17]=[C:13]3[CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.BrC1C=C2C(C(=O)C(=O)N2C)=C(C)C=1.NC1N=C2C=CC=C(N[C@@H]3CC[C@H](O)CC3)N2N=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>O1CCOCC1.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[N:14]3[N:15]=[C:16]([NH:18][C:19]4[CH:27]=[C:26]5[C:22]([CH2:23][C:24](=[O:29])[N:25]5[CH3:28])=[C:21]([CH3:31])[CH:20]=4)[N:17]=[C:13]3[CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1

Participants

8

Reactant 5

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 59276440HCID 59276440, compoundHCID 178428288HCID 178428288, compoundHCID 178508183HCID 178508183, compound

Product 1

HCID 178428287HCID 178428287, compoundYield 39.1%

Reagents, catalysts & solvents 2

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

cis-6-(5-(4-Hydroxycyclohexylamino)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)-1,4-dimethylindoline-2,3-dione. A mixture of 6-bromo-1,4-dimethylindoline-2,3-dione (0.34 g, 1.338 mmol), cis-4-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-5-ylamino)cyclohexanol (0.446 g, 1.804 mmol), cesium carbonate (1.308 g, 4.01 mmol), tris(dibenzylideneacetone) dipalladium(0) (0.245 g, 0.268 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.310 g, 0.535 mmol) in 1,4-dioxane (6 mL) was degassed for 2 min and then stirred at 90° C. for 17 h. The cooled reaction solution was filtered through Celite and the filter cake was washed with dichloromethane and methanol. The solvent was removed under reduced pressure. Purification by column chromatography (eluting with 0-10% methanol in dichloromethane) provided the title compound as a yellow solid (0.22 g, 39.1% yield). MS (ESI) m/z 421.5 [M+H]+.

Workup

  1. customwas degassed for 2 min
  2. customThe cooled reaction solution
  3. filtrationwas filtered through Celite
  4. washthe filter cake was washed with dichloromethane and methanol
  5. customThe solvent was removed under reduced pressure
  6. customPurification
  7. washby column chromatography (eluting with 0-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-5e1238b239934e7d92045acb283e9403
Source dataset
uspto-grants-2012_10
Patent number
US08299056B2

Reaction notes

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