Sodium Carbonate → (2S)-1-(4-(1-isopropyl-3-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazol-4-yl)pyrimidin-2-ylamino)propan-2-ol

HRID 500714ノート

反応式

HRID 500714 の反応式
I[C:2]1[C:6]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][CH2:14][C@@H:15]([OH:17])[CH3:16])[N:8]=2)=[CH:5][N:4]([CH:18]([CH3:20])[CH3:19])[N:3]=1.[NH:21]1[C:25]2=[N:26][CH:27]=[C:28](B(O)O)[CH:29]=[C:24]2[CH:23]=[CH:22]1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.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>[CH:18]([N:4]1[CH:5]=[C:6]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][CH2:14][C@@H:15]([OH:17])[CH3:16])[N:8]=2)[C:2]([C:28]2[CH:29]=[C:24]3[CH:23]=[CH:22][NH:21][C:25]3=[N:26][CH:27]=2)=[N:3]1)([CH3:20])[CH3:19]

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 454802571H-Pyrrolo[2,3-B]pyridin-5-ylboronic acidHCID 57856239(2S)-1-(4-(3-iodo-1-isopropyl-1H-pyrazol-4-yl)pyrimidin-2-ylamino)propan-2-ol

生成物 1

HCID 25183759(2S)-1-(4-(1-isopropyl-3-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazol-4-yl)pyrimidin-2-ylamino)propan-2-ol収率 86.1%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

実験手順

To a solution of (2S)-1-(4-(3-iodo-1-isopropyl-1H-pyrazol-4-yl)pyrimidin-2-ylamino)propan-2-ol B-1-3 (0.312 g, 0.8 mmol) in toluene (15 mL) and EtOH (5 mL) were added 1H-pyrrolo[2,3-b]pyridin-5-ylboronic acid (0.40 g, 1.6 mmol) and 2 N aq. Na2CO3 (1.24 mL), and the resulting mixture was degassed under N2 for 2 minutes. Then Pd(PPh3)4 (0.23 g, 0.2 mmol) was added and the mixture was degassed again. The resulting mixture was heated to reflux and stirred overnight. The organic layer was separated and concentrated, the residue was purified via prep HPLC to afford (2S)-1-(4-(1-isopropyl-3-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazol-4-yl)pyrimidin-2-ylamino)propan-2-ol (B-1) (0.260 g, 66.19%) as a yellow solid.

後処理

  1. customthe resulting mixture was degassed under N2 for 2 minutes
  2. customthe mixture was degassed again
  3. temperatureThe resulting mixture was heated
  4. temperatureto reflux
  5. customThe organic layer was separated
  6. concentrationconcentrated
  7. customthe residue was purified via prep HPLC

出典と根拠

ORDレコード
ord-b2ae503e32834002a49e65dfeac6609c
出典データセット
uspto-grants-2010_08
特許番号
US07772246B2

反応ノート

読み込み中…