Cesium carbonate → Tert-butyl 4-(5-(3-methoxyphenyl)-1-(phenylsulfonyl)-1h-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylate

HRID 79532Notes

Reaction equation

HRID 79532 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)=[CH:6][N:5]=[C:4]2[N:16]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH:17]=[CH:18][C:3]=12.[N:28]1([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]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+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:15][O:14][C:10]1[CH:9]=[C:8]([C:7]2[C:2]([N:31]3[CH2:30][CH2:29][N:28]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:33][CH2:32]3)=[C:3]3[CH:18]=[CH:17][N:16]([S:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)(=[O:21])=[O:20])[C:4]3=[N:5][CH:6]=2)[CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 687603871H-Pyrrolo[2,3-b]pyridine, 4-chloro-5-(3-methoxyphenyl)-1-(phenylsulfonyl)-

Product 1

HCID 68761257Tert-butyl 4-(5-(3-methoxyphenyl)-1-(phenylsulfonyl)-1h-pyrrolo[2,3-b]pyridin-4-yl)piperazine-1-carboxylateYield 29.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

4-Chloro-5-(3-methoxyphenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyri dine (0.400 g, 1.00 mmol), tert-butyl piperazine-1-carboxylate (0.280 g, 1.50 mmol), Pd(OAc)2 (0.0225 g, 0.100 mmol), Xantphos (0.0870 g, 0.150 mmol), and Cs2CO3 (0.490 g, 1.50 mmol) were placed in degassed toluene (4 mL). The mixture was heated to 100° C. for 24 hours. The reaction was cooled to room temperature, filtered through celite, and concentrated. The product was purified (500:5 to 500:7 DCM:MeOH) to yield tert-butyl 4-(5-(3-methoxyphenyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyri din-4-yl)piperazine-1-carboxylate (0.160 g, 29.0% yield).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered through celite
  3. concentrationconcentrated
  4. customThe product was purified (500:5 to 500:7 DCM:MeOH)

Sources & evidence

ORD record
ord-9485091727a042dd83558ff672d029d0
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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