Potassium Acetate → 2-((2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)methyl)cyclohexanol

HRID 74909노트

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HRID 74909 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10](B3OC(C)(C)C(C)(C)O3)=[CH:9][N:8]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[C:5]2=[N:6][CH:7]=1.Cl[C:31]1[N:36]=[C:35]([NH:37][CH2:38][C:39]2(O)[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]2)[C:34]([F:46])=[CH:33][N:32]=1.CC([O-])=[O:49].[K+]>CC(N(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:31]3[N:36]=[C:35]([NH:37][CH2:38][CH:39]4[CH2:44][CH2:43][CH2:42][CH2:41][CH:40]4[OH:49])[C:34]([F:46])=[CH:33][N:32]=3)=[CH:9][N:8]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)(=[O:21])=[O:22])[C:5]2=[N:6][CH:7]=1

참가 물질

6

반응물 3

HCID 517044Potassium AcetateHCID 575977475-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 790758021-((2-Chloro-5-fluoropyrimidin-4-ylamino)methyl)cyclohexanol2회

생성물 1

HCID 672858742-((2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)methyl)cyclohexanol

시약·촉매·용매 2

HCID 15220664Palladium--triphenylphosphane (1/1)촉매HCID 31374Dimethylacetamide용매

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온도
140 °C

실험 절차

To a degassed solution of 5-chloro-1-(p-tolylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine (0.15 g, 0.35 mmol), 1-((2-chloro-5-fluoropyrimidin-4-ylamino)methyl)cyclohexanol, 14a, (0.09 g, 0.35 mmol) and aqueous KOAc solution (1.04 mL of 1M solution, 1.04 mmol) in dimethylacetamide was added palladium triphenylphosphine (0.04 g, 0.03 mmol). The reaction mixture was heated at 140° C. in microwave for 15 min and then cooled to room temperature. The reaction mixture was filtered through celite, concentrated in vacuo, and the resulting crude residue was purified by by preparatory HPLC (0.1% TFA-H2O/acetonitrile) to afford the desired product, 14b:

후처리

  1. temperaturecooled to room temperature
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationconcentrated in vacuo
  4. customthe resulting crude residue was purified by by preparatory HPLC (0.1% TFA-H2O/acetonitrile)

출처 및 근거

ORD 기록
ord-a2462e5501d647cd957faccd3bd9c721
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829007B2

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