Sodium Carbonate → HCID 69207799, compound

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridine	HCID 24208789	—
Reactant	4-[(tert-Butoxycarbonyl)amino]cyclohex-1-en-1-yl trifluoromethanesulfonate	HCID 59832199	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 69207799	HCID 69207799	96%

Reaction Conditions

Temperature	80 °C

Reaction Steps

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).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07446199B2
Source dataset	uspto-grants-2008_11
ORD ID	ord-73f5169ad36b45eb8b632d08204f4de8
Source note	uspto-grants-2008_11