Cesium carbonate → HCID 118114536, compound

HRID 1050571Notes

Reaction equation

HRID 1050571 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:16](=[O:23])([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[NH2:17].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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:14]([C:8]1([C:5]2[CH:6]=[CH:7][C:2]([NH:17][C:16](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:3][CH:4]=2)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)#[N:15]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 77922tert-Butyl carbamateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 658143784-(4-Bromophenyl)piperidine-4-carbonitrile

Product 1

HCID 118114536HCID 118114536, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
115 °C

Procedure

The mixture of 4-(4-bromophenyl)piperidine-4-carbonitrile (347, 520 mg, 1.96 mmol), tert-butyl carbamate (460 mg, 3.92 mmol), Pd2(dba)3 (180 mg, 0.20 mmol), XantPhos (350 mg, 0.60 mmol), fine-powder Cs2CO3 (1.96 g, 6.0 mmol) in 30 mL dioxane was degassed using N2 stream for 5 min and stirred in 115° C. bath in N2 atmosphere for overnight. It was cooled to RT, diluted with EtOAc 200 mL and filtered. The filtrate was concentrated in vacuo and subjected to silica flash column using 0 to 30% MeOH in DCM to afford tert-butyl 4-(4-cyanopiperidin-4-yl)phenylcarbamate (348, 230 mg, 39%).

Workup

  1. customwas degassed
  2. customfor 5 min
  3. temperatureIt was cooled to RT
  4. additiondiluted with EtOAc 200 mL
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-0a913e8f101340d6bdc6ad81549d2a00
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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