proline dl-form → HCID 54445738, 화합물

HRID 849261

반응식

HRID 849261 반응식
N1C[CH2:7][CH2:6][CH:2]1[C:3](O)=O.[C:9]([O-:12])([O-])=[O:10].[K+].[K+].CC[N:17](CC)CC.[Br-].C([NH+](CC)CC)C.BrC1C=[CH:35][C:34]([Br:37])=[CH:33][C:32]=1[F:38].C([O-])([O-])=O.[K+].[K+].CCO[CH2:48][CH3:49]>[Cu]I.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.CN(C=O)C.O>[F:38][C@@:32]1([C:9]([OH:12])=[O:10])[CH2:33][CH:34]([Br:37])[CH2:35][N:17]1[C:49]1[CH:48]=[CH:7][CH:6]=[CH:2][CH:3]=1

참가 물질

10

반응물 6

HCID 614proline dl-formHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 12493Triethylamine hydrobromideHCID 1370041,4-Dibromo-2-fluorobenzeneHCID 86755020HCID 86755020, 화합물

생성물 1

HCID 54445738HCID 54445738, 화합물

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 21962138N,N-Dimethylformamide--water (1/1)용매

반응 조건

온도
120 °C

실험 절차

To a solution of DL-proline (576 mg, 5 mmol) in 10/1 DMF-H2O (7.5 ml) at RT were added CuI (48 mg, 0.25 mmol), Pd(PPh3)4 (290 mg, 0.25 mmol), K2CO3 (690 mg, 5 mmol), NEt3 (1.4 ml, 10 mmol), triethylammonium bromide (158 mg, 0.75 mmol), and 1,4-dibromo-2-fluorobenzene. The resulting mixture was stirred in a sealed tube at 120° C. for 48 hours. The reaction mixture was cooled to room temperature and poured onto saturated K2CO3 /Et2O. The aqueous layer was extracted 3× with Et2O. The pH of the aqueous layer was adjusted to 4 and extracted 3× with EtOAc. The combined organics were washed with brine, dried over MgSO4, and concentrated in vacuo to produce title compound which was used without further purification: LCMS (M+1)=287. ##STR393##

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe aqueous layer was extracted 3× with Et2O
  3. extractionextracted 3× with EtOAc
  4. washThe combined organics were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-8ddff6181fa046e180dda31bb25f3ba9
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06011059

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