Cesium carbonate → HCID 118114536, 화합물

HRID 1050571노트

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HRID 1050571 반응식
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]

참가 물질

7

반응물 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

생성물 1

HCID 118114536HCID 118114536, 화합물수율 39%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

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온도
115 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-0a913e8f101340d6bdc6ad81549d2a00
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382246B2

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