Sodium Carbonate → 5-[2-(4-{1-[(Tert-butoxycarbonyl)amino]cyclobutyl}phenyl)-3-phenylpyrimido[1,2-b]indazol-8-yl]pyrazole-1-carboxylic acid tert-butyl ester

HRID 877050ノート

反応式

HRID 877050 の反応式
[C:1]([O:5][C:6](=[O:38])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:31]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:30][N:21]4[N:22]=[C:23]5[C:28]([CH:27]=[CH:26][C:25](Br)=[CH:24]5)=[C:20]4[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:39]([O:43][C:44]([N:46]1[C:50](B(O)O)=[CH:49][CH:48]=[N:47]1)=[O:45])([CH3:42])([CH3:41])[CH3:40].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[C:39]([O:43][C:44]([N:46]1[C:50]([C:25]2[CH:26]=[CH:27][C:28]3[C:23]([CH:24]=2)=[N:22][N:21]2[CH:30]=[C:31]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:18]([C:15]4[CH:16]=[CH:17][C:12]([C:8]5([NH:7][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:38])[CH2:11][CH2:10][CH2:9]5)=[CH:13][CH:14]=4)=[N:19][C:20]=32)=[CH:49][CH:48]=[N:47]1)=[O:45])([CH3:42])([CH3:40])[CH3:41]

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 467389241H-Pyrazole-5-boronic acid, N1-BOC protectedHCID 86702528{1-[4-(8-Bromo-3-phenylpyrimido[1,2-b]indazol-2-yl)phenyl]-cyclobutyl}carbamic acid tert-butyl ester

生成物 1

HCID 679912345-[2-(4-{1-[(Tert-butoxycarbonyl)amino]cyclobutyl}phenyl)-3-phenylpyrimido[1,2-b]indazol-8-yl]pyrazole-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 3

HCID 178477754HCID 178477754、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
105 °C

実験手順

100 mg (0.18 mmol) {1-[4-(8-Bromo-3-phenylpyrimido[1,2-b]indazol-2-yl)phenyl]-cyclobutyl}carbamic acid tert-butyl ester, intermediate example Int-2-2, 74.5 mg (0.35 mmol) [1-(tert-butoxycarbonyl)-1H-pyrazol-5-yl]boronic acid, 14.3 mg (0.02 mmol) 1,1 bis(diphenylphosphino)ferrocenedichloro-palladium(II) and 55.8 mg (0.53 mmol) sodium carbonate in 1.8 mL dioxane and 0.3 mL water (both solvents had been degassed) were heated in the microwave for 30′ at 105° C. The reaction mixture was poured on water/dichloromethane/saturated ammonium chloride and vigorously stirred for 30′. The organic phase was separated, washed twice with brine, dried (sodium sulfate) and filtrated. The solvent was evaporated and the crude residue (181 mg>100%) was used in the next step without further purification.

後処理

  1. additionThe reaction mixture was poured on water/dichloromethane/saturated ammonium chloride
  2. customThe organic phase was separated
  3. washwashed twice with brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltrated
  6. customThe solvent was evaporated
  7. customthe crude residue (181 mg>100%) was used in the next step without further purification

出典と根拠

ORDレコード
ord-f78e78a895674c169e1203c6207284a3
出典データセット
uspto-grants-2015_03
特許番号
US08987286B2

反応ノート

読み込み中…