Cesium carbonate → HCID 68703896、化合物

HRID 220094ノート

反応式

HRID 220094 の反応式
[NH2:1][C:2]1[N:6]([C:7]2[N:12]=[CH:11][N:10]=[C:9]([NH:13][CH3:14])[CH:8]=2)[N:5]=[C:4]([CH3:15])[CH:3]=1.[F:16][C:17]([C:20]1[CH:21]=[C:22]([NH:26][C:27](=[O:36])[C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[C:30](I)[CH:29]=2)[CH:23]=[N:24][CH:25]=1)([CH3:19])[CH3:18].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:16][C:17]([C:20]1[CH:21]=[C:22]([NH:26][C:27](=[O:36])[C:28]2[CH:29]=[CH:30][C:31]([CH3:34])=[C:32]([NH:1][C:2]3[N:6]([C:7]4[CH:8]=[C:9]([NH:13][CH3:14])[N:10]=[CH:11][N:12]=4)[N:5]=[C:4]([CH3:15])[CH:3]=3)[CH:33]=2)[CH:23]=[N:24][CH:25]=1)([CH3:19])[CH3:18]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 591733071018473-23-8HCID 68704215HCID 68704215、化合物

生成物 1

HCID 68703896HCID 68703896、化合物収率 64%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
150 °C

実験手順

A suspension of [6-(5-amino-3-methyl-pyrazol-1-yl)-pyrimidin-4-yl]-methyl-amine (17 mg, 0.083 mmol), N-[5-(1-fluoro-1-methyl-ethyl)-pyridin-3-yl]-3-iodo-4-methyl-benzamide (41 mg, 0.104 mmol), Pd(OAc)2 (2 mg, 0.009 mmol), Xantphos (9 mg, 0.0166 mmol) and Cs2CO3 (54 mg, 0.166 mmol) in anhydrous 1,4-dioxane (2 mL) in a pressure vial was degassed by a stream of argon and sealed. The reaction was stirred at 150° C. for 1 hour. LCMS showed completion of the reaction. A solution of 5% diethyl dithiocarbomic acid sodium salt (3 mL) was added to the reaction. A light yellow precipitate was collected by filtration, washed with water and dried. The crude was purified by column (SiO2, EtOAc/hexanes: 30 to 100%) to give a white solid (25 mg, 64%): m/z 475.2 (M+1).

後処理

  1. customwas degassed by a stream of argon
  2. customsealed
  3. customcompletion of the reaction
  4. additionA solution of 5% diethyl dithiocarbomic acid sodium salt (3 mL) was added to the reaction
  5. filtrationA light yellow precipitate was collected by filtration
  6. washwashed with water
  7. customdried
  8. customThe crude was purified by column (SiO2, EtOAc/hexanes: 30 to 100%)

出典と根拠

ORDレコード
ord-8387268ab6f24314a29d134cf3d0cbfa
出典データセット
uspto-grants-2012_06
特許番号
US08202876B2

反応ノート

読み込み中…