Potassium Carbonate → (R)-tert-butyl 3-(4-chlorophenyl)-1-oxo-1-(4-(5-phenyl-1H-pyrrolo [2,3-b]pyridin-4-yl)piperazin-1-yl)propan-2-ylcarbamate

HRID 79538노트

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HRID 79538 반응식
Br[C:2]1[C:3]([N:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:35])[C@H:18]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[CH2:13][CH2:12]2)=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[C:36]1(B(O)O)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][C@@H:18]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:32])([CH3:31])[CH3:33])[C:17](=[O:35])[N:14]2[CH2:15][CH2:16][N:11]([C:3]3[C:2]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[CH:7][N:6]=[C:5]4[NH:8][CH:9]=[CH:10][C:4]=34)[CH2:12][CH2:13]2)=[CH:25][CH:24]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 68763825(R)-tert-Butyl 1-(4-(5-bromo-1H-pyrrolo [2,3-b]pyridin-4-yl)piperazin-1-yl)-3-(4-chlorophenyl)-1-oxopropan-2-ylcarbamate

생성물 1

HCID 68761687(R)-tert-butyl 3-(4-chlorophenyl)-1-oxo-1-(4-(5-phenyl-1H-pyrrolo [2,3-b]pyridin-4-yl)piperazin-1-yl)propan-2-ylcarbamate수율 10%

시약·촉매·용매 1

HCID 178418397HCID 178418397, 화합물촉매

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온도
80 °C

실험 절차

(R)-tert-Butyl 1-(4-(5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-(4-chlorophenyl)-1-oxopropan-2-ylcarbamate (0.180 g, 0.320 mmol, see Example 1), phenylboronic acid (0.0468 g, 0.384 mmol), Pd(PPh3)4 (0.0185 g, 0.0160 mmol) and 10% K2CO3 (aq., 0.66 mL, 0.47 mmol) were added to an Ar degassed solution of 2:1 toluene:EtOH (3 mL). The reaction was then heated to 80° C. overnight. The reaction was then cooled to room temperature, diluted with water, and extracted with DCM. The organic fractions were dried, filtered, concentrated, and purified (500:10-500:15) to give (R)-tert-butyl 3-(4-chlorophenyl)-1-oxo-1-(4-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)propan-2-ylcarbamate (0.018 g, 10.0% yield).

후처리

  1. customdegassed solution of 2:1 toluene
  2. temperatureThe reaction was then cooled to room temperature
  3. additiondiluted with water
  4. extractionextracted with DCM
  5. customThe organic fractions were dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified (500:10-500:15)

출처 및 근거

ORD 기록
ord-4c862b85839c402c9f84e0afe6424c93
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841304B2

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