Dimethylformamide → HCID 58615384, compound

HRID 853031Notes

Reaction equation

HRID 853031 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22](I)[CH:23]=3)[N:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C([SiH](CCCCCC)CCCCCC)CCCCC.[C]=O.CN([CH:57]=[O:58])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([CH:57]=[O:58])[CH:23]=3)[N:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 76231CID 76231HCID 58615400HCID 58615400, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 58615384HCID 58615384, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

The similar procedure as described in Example 10b was used, starting from 4-(6-iodo-quinolin-4-yloxy)-piperidine-1-carboxylic acid tert-butyl ester (example 48a), diphenylpropyl phsophine, palladium acetate, triethyl amine, and trihexylsilane in anhydrous DMF (25 ml) was charged with carbon monoxide at 75 psi to give 4-(6-formyl-quinolin-4-yloxy)-piperidine-1-carboxylic acid tert-butyl ester. LC-MS m/e 357 (MH+).

Sources & evidence

ORD record
ord-edb31175ce374aa7af51f8ef93f64c43
Source dataset
uspto-grants-2007_08
Patent number
US07253285B2

Reaction notes

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