Cesium carbonate → HCID 86685941, compound

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1,2-Diaminocyclohexane, (+)-	HCID 479307	—
Reactant	(5-Bromo-3-pyridinyl)methanol	HCID 2784733	—
Reactant	2-Chloro-7,7-dimethyl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one	HCID 71743819	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Water	HCID 962	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 86685941	HCID 86685941	92%

Reaction Steps

2-Chloro-7,7-dimethyl-6,7-dihydro-pyrrolo[3,4-b]pyridin-5-one (intermediate A-16 [G], 39.2 mg, 0.2 mmol), (5-bromo-pyridin-3-yl)-methanol (example 3 [A], 74.8 mg, 0.4 mmol), CuI (3.8 mg, 0.02 mmol), (1S,2S)-cyclohexane-1,2-diamine (4.5 mg, 0.04 mmol) and Cs2CO3 (130 mg, 0.4 mmol) were dissolved in dioxane (5 mL). The reaction mixture was subjected to microwave reaction at 140° C. for 1 hours before it was poured into H2O (50 mL) and extracted with EtOAc (2×25 mL). The organic layer was washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product (55.7 mg, 92%) as solid. MS: 304.1 (M+H+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09133158B2
Source dataset	uspto-grants-2015_09
ORD ID	ord-4f8ff79e519f46f6b245f37526ba302a
Source note	uspto-grants-2015_09