2-Bromo-4-methylpyridine → (3-(1-Hydroxyethyl)-1-(5-(4-methylpyridin-2-yl)pyrimidin-2-yl)-1H-indol-6-yl)(morpholino)methanone

Participants

Role	Name	HCID	Charge
Reactant	2-Bromo-4-methylpyridine	HCID 2734087	—
Reactant	1-(5-(2-Fluorophenyl)pyrimidin-2-yl)-6-(morpholine-4-carbonyl)-1H-indole-3-carbaldehyde	HCID 118666041	—
Reactant	(1-(5-Bromopyrimidin-2-yl)-3-(hydroxymethyl)-1H-indol-6-yl)(morpholino)methanone	HCID 118666263	—
Reactant	(1-(5-(2-Fluorophenyl)pyrimidin-2-yl)-3-(1-hydroxyethyl)-1H-indol-6-yl)(morpholino)-methanone	HCID 118666316	—
Product	(3-(1-Hydroxyethyl)-1-(5-(4-methylpyridin-2-yl)pyrimidin-2-yl)-1H-indol-6-yl)(morpholino)methanone	HCID 118666164	—

Reaction Steps

(1-(5-Bromopyrimidin-2-yl)-3-(hydroxymethyl)-1H-indol-6-yl)(morpholino)methanone (intermediate 27c) was converted into a boronic ester that was subsequently reacted with 2-bromo-4-methylpyridine under Suzuki conditions. The resulting product was oxidized to the corresponding aldehyde and then submitted to a Grignard reaction analogously to the protocols 28a) and 28b), respectively. Light yellow solid. Yield: 70 mg

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09315490B2
Source dataset	uspto-grants-2016_04
ORD ID	ord-87961ad6e5d248be8c8ca2acc68079c2
Source note	uspto-grants-2016_04