Cesium carbonate → HCID 86646542, compound

HRID 2387234Notes

Reaction equation

HRID 2387234 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][C:10](=[O:14])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Br[C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][N:17]=1.C([O-])([O-])=O.[Cs+].[Cs+].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>O1CCOCC1.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[O:14]=[C:10]1[N:11]([C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][N:17]=2)[CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 27815432-Bromo-4-(trifluoromethyl)pyridineHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylate

Product 1

HCID 86646542HCID 86646542, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1-Boc-3-oxopiperazine (1.0 eq.), 2-bromo-4-(trifluoromethyl)pyridine (1.5 eq.) and Cs2CO3(1.5 eq.) in 1,4-dioxane (0.5M) was degassed under Argon flow for 30 min, then Pd(OAc)2(0.1 eq.) and Xantphos (0.15 eq.) were added, the vial was sealed and stirring was continued at 110° C. for 18 hr. Reaction mixture was diluted with EtOAc and filtered through a pad of SolcaFloc® 200 FCC. After removal of the solvent, the crude product was purified by flash column chromatography on silica gel using 10-40% EtOAc/Petroleum ether as eluent to afford the desired product I1 as yellow solid (92% yield). 1H NMR (400 MHz, CDCl3, 300K) δ 8.57 (1H, d, J=4.8 Hz), 8.40 (1H, bs), 7.32 (1H, d, J=4.8 Hz), 4.31 (2H, s), 4.17 (2H, t, J=5.3 Hz), 3.76 (2H, t, J=5.3 Hz), 1.50 (9H, s). MS (ES) C15H18F3N3O3 requires: 345, found: 346 (M+H)+.

Workup

  1. customwas degassed under Argon flow for 30 min
  2. customthe vial was sealed
  3. customReaction mixture
  4. filtrationfiltered through a pad of SolcaFloc® 200 FCC
  5. customAfter removal of the solvent
  6. customthe crude product was purified by flash column chromatography on silica gel using 10-40% EtOAc/Petroleum ether as eluent

Sources & evidence

ORD record
ord-cb12518200ff414a8cd1f7e3abcfdfca
Source dataset
uspto-grants-2012_09
Patent number
US08268827B2

Reaction notes

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