3-Bromopyridine-2-carboxylic Acid → cis-6-Methoxy-5-methyl-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridine

HRID 455376

Reaction equation

HRID 455376 reaction equation
Br[C:2]1[C:3]([C:8](O)=O)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:11][O:12][C:13]1[C:14]([CH3:28])=[C:15](B2OC(C)(C)C(C)(C)O2)[CH:16]=[CH:17][CH:18]=1>>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]2[CH2:8][C@H:3]3[C@@H:2]([C:15]=2[C:14]=1[CH3:28])[CH2:7][CH2:6][CH2:5][NH:4]3

Participants

3

Reactant 2

HCID 20501293-Bromopyridine-2-carboxylic Acid2×HCID 205806672-(3-Methoxy-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 67222612cis-6-Methoxy-5-methyl-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridine

Procedure

The title compound is prepared from 3-bromo-pyridine-2-carboxylic acid and 2-(3-methoxy-2-methyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (may be prepared as in WO 2001053268 described) following the synthetic sequence and protocols described for Intermediate 41; since 3-bromo-pyridine-2-carboxylic acid instead of 3-bromo-pyridine-2-carbonitrile is used for the Suzuki-Miyaura coupling (Step 1 of Intermediate 41), hydrolysis of the nitrile (Step 2 of Intermediate 41) is omitted.

Sources & evidence

ORD record
ord-68c53908be3a4877b8b0e1664dd4ec15
Source dataset
uspto-grants-2013_07
Patent number
US08497281B2

Linked notes

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