N,N-Dimethylglycine → 3-(1-Methyl-1H-pyrazol-4-yl)-5-phenylsulfanyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1991102노트

반응식

HRID 1991102 반응식
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:12]=[N:13][N:14]([C:16](C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:15]=3)=[CH:9][N:8]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])[C:5]2=[N:6][CH:7]=1.[C:43]1([SH:49])[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.CN(C)CC(O)=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.[Cu]I>[CH3:16][N:14]1[CH:15]=[C:11]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([S:49][C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[CH:3]=3)[N:8]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:40])[CH3:41])[CH:9]=2)[CH:12]=[N:13]1

참가 물질

7

반응물 4

HCID 673N,N-DimethylglycineHCID 7969ThiophenolHCID 62657Potassium Phosphate, TribasicHCID 591286885-Bromo-1-(2-trimethylsilanyl-ethoxymethyl)-3-(1-trityl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 591865873-(1-Methyl-1H-pyrazol-4-yl)-5-phenylsulfanyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

A mixture of 22 (50 mg, 0.079 mmol), benzenethiol (13.0 mg, 0.118 mmol), copper (I) iodide (3.0 mg, 0.016 mmol), N,N-dimethylglycine (1.62 mg, 0.016 mmol) and potassium phosphate (41.8 mg, 0.197 mmol) in DMF (0.5 mL) were heated at 120° C. for 69 h. The reaction mixture was cooled and partitioned between AcOEt/brine, the layers separated and the aqueous phase extracted with more AcOEt (2×). The combined organic extracts were dried (MgSO4) and concentrated. The resulting crude residue containing 23 was used for the subsequent deprotection step.

후처리

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between AcOEt/brine
  3. customthe layers separated
  4. extractionthe aqueous phase extracted with more AcOEt (2×)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. concentrationconcentrated
  7. additionThe resulting crude residue containing 23

출처 및 근거

ORD 기록
ord-5ecd8133a2d744029393622811a89cea
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07645769B2

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