Carbon Dioxide → HCID 66643533, compound

HRID 44673Notes

Reaction equation

HRID 44673 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:9]=[CH:10][C:3]=12.[C:30](=[O:32])=[O:31].[Cl-].[NH4+]>C1COCC1.CCOC(C)=O>[C:11]([N:8]1[C:4]2[N:5]=[CH:6][CH:7]=[C:2]([C:30]([OH:32])=[O:31])[C:3]=2[CH:10]=[N:9]1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 25517Ammonium ChlorideHCID 579696964-iodo-1-trityl-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 66643533HCID 66643533, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Isopropylmagnesium chloride-lithium chloride complex (21.99 mL of 14% w/v, 21.20 mmol) in THF (2.5 mL) was cooled to below −20° C. This was treated with 4-iodo-1-trityl-pyrazolo[5,4-b]pyridine (9.84 g, 20.19 mmol) under nitrogen and allowed to stir for 30 minutes. The reaction was then treated with 3 pellets of CO2 and allowed to warm up. After a further hour the mixture was diluted with EtOAc and acidified with saturated aqueous ammonium chloride. The layers were separated, dried (MgSO4), filtered and concentrated in vacuo. The mixture was purified by column chromatography (1:1 Petroleum ether/EtOAc moving to 10% MeOH/EtOAc) to give the product as an off-white oil (7.0 g, 86% Yield). 1H NMR (DMSO, 400 MHz) δ 7.17-7.26 (15H, m), 7.47-7.49 (1H, m), 8.18 (1H, d), 8.56-8.58 (1H, m).

Workup

  1. temperatureto warm up
  2. customThe layers were separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe mixture was purified by column chromatography (1:1 Petroleum ether/EtOAc moving to 10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-597d040693ad48719ec42fc4ebe4993d
Source dataset
uspto-grants-2013_09
Patent number
US08541445B2

Reaction notes

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