Water → (S)-tert-butyl (1-(4-amino-5-(quinolin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)but-3-en-2-yl)carbamate

HRID 336161노트

반응식

HRID 336161 반응식
[NH2:1][C:2]1[C:3]2[C:10](I)=[CH:9][N:8]([CH2:12][C@@H:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:14]=[CH2:15])[C:4]=2[N:5]=[CH:6][N:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CO[CH2:32][CH2:33]OC.O.C(O[CH2:41][CH3:42])(=O)C>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[NH2:1][C:2]1[C:3]2[C:10]([C:10]3[CH:9]=[N:8][C:4]4[C:32]([CH:33]=3)=[CH:42][CH:41]=[CH:2][CH:3]=4)=[CH:9][N:8]([CH2:12][C@@H:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:14]=[CH2:15])[C:4]=2[N:5]=[CH:6][N:7]=1

참가 물질

7

반응물 5

HCID 962Water2회HCID 80711,2-DimethoxyethaneHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 86711293HCID 86711293, 화합물

생성물 1

HCID 86711294(S)-tert-butyl (1-(4-amino-5-(quinolin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)but-3-en-2-yl)carbamate

시약·촉매·용매 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매

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온도
100 °C

실험 절차

A mixture of (S)-tert-butyl (1-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)but-3-en-2-yl)carbamate (8.26 g) obtained in Step 2,3-quinolineboronic acid (4.99 g), cesium carbonate (12.54 g), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride (785.6 mg), DME (66 ml), and water (33 ml) was stirred under a nitrogen atmosphere at 100° C. for 2 hours. After cooling the reaction mixture, water and ethyl acetate were added thereto to separate the organic layer. The aqueous layer was then extracted with ethyl acetate twice. The resulting organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate, ethyl acetate/methanol) to obtain the title compound (8.0 g) as a light-orange solid.

후처리

  1. additionwere added
  2. customto separate the organic layer
  3. extractionThe aqueous layer was then extracted with ethyl acetate twice
  4. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate, ethyl acetate/methanol)

출처 및 근거

ORD 기록
ord-e256dd50faa34f708c6c8561af5f2490
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889666B2

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