Tris(1,1-dimethylethyl)phosphine → HCID 58531046, compound

HRID 1878542Notes

Reaction equation

HRID 1878542 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:23]=[C:11]3[N:12]=[C:13]([Cl:22])[CH:14]=[C:15]([N:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)[N:10]3[N:9]=2)=[CH:4][CH:3]=1.CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[N:43]1([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1>C1(C)C=CC=CC=1.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[C:52]([O:51][C:49]([N:43]1[CH2:48][CH2:47][N:46]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:23]=[C:11]4[N:12]=[C:13]([Cl:22])[CH:14]=[C:15]([N:16]5[CH2:21][CH2:20][O:19][CH2:18][CH2:17]5)[N:10]4[N:9]=3)=[CH:4][CH:3]=2)[CH2:45][CH2:44]1)=[O:50])([CH3:55])([CH3:53])[CH3:54]

Participants

7

Reactant 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 23676156Sodium t-butoxideHCID 58531012HCID 58531012, compound

Product 1

HCID 58531046HCID 58531046, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 1140TolueneSolvent2×

Procedure

There was dissolved, in toluene (3 mL), 2-(4-bromo-phenyl)-5-chloro-7-morpholin-4-yl-pyrazolo[1,5-a]pyrimidine (56.2 mg, 0.143 mM) in an argon gas atmosphere, then there were added, to the resulting solution, a solution of sodium t-butoxide (20.6 mg, 0.215 mM), tris(dibenzylidene acetone) di-palladium (7.2 mg, 0.0079 mM) and tri-t-butyl phosphine (4.7 μL, 0.023 mM) in toluene (0.30 mL) and t-butyl 1-piperazine carboxylate (39.9 mg, 0.215 mM) and the resulting mixture was stirred at 90° C. for 30 minutes. This reaction liquid was diluted with a saturated aqueous common salt solution and then extracted with ethyl acetate. The extracts thus obtained were combined, dried over anhydrous sodium sulfate, then the solvent was distilled off and the resulting residue was purified by the silica gel column chromatography (ethyl acetate/hexane=1:3) to thus give the title compound (40.5 mg, yield: 57%).

Workup

  1. customThis reaction liquid
  2. additionwas diluted with a saturated aqueous common salt solution
  3. extractionextracted with ethyl acetate
  4. customThe extracts thus obtained
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off
  7. customthe resulting residue was purified by the silica gel column chromatography (ethyl acetate/hexane=1:3)

Sources & evidence

ORD record
ord-d66ca0fed3a84dcca20231bca1d5b547
Source dataset
uspto-grants-2012_11
Patent number
US08314098B2

Reaction notes

Loading…