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

HRID 526933ノート

反応式

HRID 526933 の反応式
[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

参加物

6

反応物 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)cyclohexanol2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 15220664Palladium--triphenylphosphane (1/1)触媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
140 °C

実験手順

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: LCMS RT=2.6 (M+1) 530.3.

後処理

  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)

出典と根拠

ORDレコード
ord-6cd869130f5b48a78af13c52c6efd5bf
出典データセット
uspto-grants-2016_05
特許番号
US09345708B2

反応ノート

読み込み中…