Cesium carbonate → HCID 68703896, compound

HRID 220094Notes

Reaction equation

HRID 220094 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 68703896HCID 68703896, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

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).

Workup

  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%)

Sources & evidence

ORD record
ord-8387268ab6f24314a29d134cf3d0cbfa
Source dataset
uspto-grants-2012_06
Patent number
US08202876B2

Reaction notes

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