Sodium Carbonate → tert-Butyl 6-(pyridin-4-yl)indoline-1-carboxylate

HRID 1628291노트

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HRID 1628291 반응식
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:4][CH:3]=1.[N:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C=O)C>[N:18]1[CH:23]=[CH:22][C:21]([C:2]2[CH:10]=[C:9]3[C:5]([CH2:6][CH2:7][N:8]3[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:4][CH:3]=2)=[CH:20][CH:19]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 22038386tert-Butyl 6-bromoindoline-1-carboxylate

생성물 1

HCID 69620888tert-Butyl 6-(pyridin-4-yl)indoline-1-carboxylate수율 41%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 6228Dimethylformamide용매

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온도
70 °C

실험 절차

To a 20 ml vial was added tert-butyl 6-bromoindoline-1-carboxylate 50.A (500 mg, 1.7 mmole), 4-pyridylboronic acid (309 mg, 2.5 mmol), tetrakis(triphenylphosphine) palladium(388, 0.34 mmol), DMF and 3 ml of saturated sodium carbonate. The reaction was stirred at 70° C. for 6 hours at which time the reaction mixture was partitioned between 300 ml EtAc and 200 ml of water. The organic solvent was removed by rotary evaporation and the crude product purified by reverse phase preparative HPLC to give tert-butyl 6-(pyridin-4-yl)indoline-1-carboxylate 50.B as a yellow solid (202 mg, 41% yield).

후처리

  1. customwas partitioned between 300 ml EtAc and 200 ml of water
  2. customThe organic solvent was removed by rotary evaporation
  3. customthe crude product purified by reverse phase preparative HPLC

출처 및 근거

ORD 기록
ord-42a8990ab842480da2e9a5031f646b37
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785468B2

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