Cesium carbonate → HCID 68703896, 화합물

HRID 220094노트

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HRID 220094 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 68703896HCID 68703896, 화합물수율 64%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매

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온도
150 °C

실험 절차

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).

후처리

  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%)

출처 및 근거

ORD 기록
ord-8387268ab6f24314a29d134cf3d0cbfa
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202876B2

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