Cesium carbonate → HCID 89612102, compound

HRID 402961Notes

Reaction equation

HRID 402961 reaction equation
Br[C:2]1[CH:3]=[C:4]([Cl:12])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[NH2:13][C:14]1[N:19]=[CH:18][C:17]([C:20]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[O:21])=[CH:16][CH:15]=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+]>O1CCOCC1>[Cl:12][C:4]1[CH:5]=[C:6]2[C:11](=[C:2]([NH:13][C:14]3[N:19]=[CH:18][C:17]([C:20]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[O:21])=[CH:16][CH:15]=3)[CH:3]=1)[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 218182138-Bromo-6-chloroquinolineHCID 59259223(6-Aminopyridin-3-yl)(morpholino)methanone

Product 1

HCID 89612102HCID 89612102, compoundYield 110.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 8-bromo-6-chlorquinoline (140 mg, 0.56 mmol), (6-aminopyrdin-3-yl)(morpholino)methanone (92 mg, 0.44 mmol), xantphos (38.5 mg, 0.067 mmol) and cesium carbonate was taken up in dry dioxane (6.5 ml). The reaction flask is evacuated and back-filled with argon (repeated 5 times). Tris(dibenzylidenacetone)palladium (0) (31 mg, 0.033 mmol) was added and the flask was evacuated and back-filled with argon (repeated 3 times). The material was heated to 90° C. (oil bath) under argon for 14 hours. The reaction mixture was cooled to ambient temperature and filtered through a short plug of celite, rinsing well with dioxane. The solvent was removed and the resulting residue loaded onto 2 preparative thin layer chromatography plates. The plates were eluted with 75% ethyl acetate/hexane and the product band collected. This provided the desired product as a light brown viscous oil (180 mg).

Workup

  1. customThe reaction flask is evacuated
  2. additionback-filled with argon (repeated 5 times)
  3. customthe flask was evacuated
  4. additionback-filled with argon (repeated 3 times)
  5. temperatureThe reaction mixture was cooled to ambient temperature
  6. filtrationfiltered through a short plug of celite
  7. washrinsing well with dioxane
  8. customThe solvent was removed
  9. washThe plates were eluted with 75% ethyl acetate/hexane
  10. customthe product band collected

Sources & evidence

ORD record
ord-6cd3405b1b1747b4828d2a7a40ba5d37
Source dataset
uspto-grants-2014_06
Patent number
US08742098B2

Reaction notes

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