Stannane, tributyl(1-ethoxyethenyl)- → HCID 66896579, compound

HRID 1913222Notes

Reaction equation

HRID 1913222 reaction equation
[CH3:1][Si:2]([CH3:51])([CH3:50])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:42][O:43][CH2:44][CH2:45][Si:46]([CH3:49])([CH3:48])[CH3:47])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:21][CH:22]=3)=[C:12]2[N:11]=[C:10]([CH2:29][CH:30]2[CH2:35][CH2:34][CH:33]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:32][CH2:31]2)[C:9]=1Br.C([Sn](CCCC)(CCCC)[C:57]([O:59][CH2:60][CH3:61])=[CH2:58])CCC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[CH3:1][Si:2]([CH3:51])([CH3:50])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:42][O:43][CH2:44][CH2:45][Si:46]([CH3:49])([CH3:48])[CH3:47])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:21][CH:22]=3)=[C:12]2[N:11]=[C:10]([CH2:29][CH:30]2[CH2:35][CH2:34][CH:33]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:32][CH2:31]2)[C:9]=1[C:57]([O:59][CH2:60][CH3:61])=[CH2:58]

Participants

5

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 69929544HCID 69929544, compound

Product 1

HCID 66896579HCID 66896579, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a 2-5 mL microwave vessel was charged ethyl 4-((7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-bromo-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)methyl)cyclohexanecarboxylate (Int-4m, 150 mg, 0.19 mmol), Pd(PPh3)4 (33 mg, 0.029 mmol), tributyl (1-ethoxyvinyl)tin (190 μL, 0.56 mmol), and 1,4-dioxane (2 mL). The vial was flushed with argon and sealed. The reaction was heated to 100° C. for 18 hours. After 18 hours, the solvent was removed in vacuo and the residue was purified via silica gel chromatography to yield the title compound. Yield=113 mg.

Workup

  1. customThe vial was flushed with argon
  2. customsealed
  3. customthe solvent was removed in vacuo
  4. customthe residue was purified via silica gel chromatography

Sources & evidence

ORD record
ord-c52c79cd23f648ad9e0a77297f492665
Source dataset
uspto-grants-2013_12
Patent number
US08609675B2

Reaction notes

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