Ethyl Acetate → HCID 59832320, compound

HRID 269509Notes

Reaction equation

HRID 269509 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][CH:8]1[CH2:13][CH2:12][C:11]([C:14]2[CH:15]=[C:16]3[CH:22]=[CH:21][NH:20][C:17]3=[N:18][CH:19]=2)=[CH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].CCOC(C)=O>[Pd].CO>[C:1]([O:5][C:6](=[O:23])[NH:7][CH:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:15]=[C:16]3[CH:22]=[CH:21][NH:20][C:17]3=[N:18][CH:19]=2)[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 69207799HCID 69207799, compound

Product 1

HCID 59832320HCID 59832320, compoundYield 92.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of trifluoro-methanesulfonic acid 4-tert-butoxycarbonylamino-cyclohex-1-enyl ester (730 mg, 20 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (490 mg, 20 mmol), Pd(dppf)Cl2 (80 mg) and 2.0M Na2CO3 (3 ml, 6 mmol) in DMF (20 ml) was heated at 80° C. under N2 for 3 hours, and then concentrated. The residue was suspended in water, filtered and the solid was purified by FC to give [4-(1H-Pyrrolo[2,3-b]pyridin-5-yl)-cyclohex-3-enyl]-carbamic acid tert-butyl ester (600 mg) in 96% yield. FIA-MS: m/e=314.05 (M+H). A suspension of the above cyclohexene (300 mg) and 10% Pd/C (200 mg) in a 1:1 mixed solvent of EtOAc and MeOH (30 ml) was shaken under 50 psi H2 for 20 h. Filtration gave [4-(1H-pyrrolo[2,3-b]pyridin-5-yl)-cyclohexyl]-carbamic acid tert-butyl ester (280 mg). FIA-MS: m/e=316.3 (M+H).

Workup

  1. filtrationFiltration

Sources & evidence

ORD record
ord-e8265413fe3e4b098ab261b05ae94071
Source dataset
uspto-grants-2008_11
Patent number
US07446199B2

Reaction notes

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