3-Hydroxypiperidine → 1-(5-((S)-1-Aminoethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)piperidin-3-ol

HRID 2205599Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[N:13]([CH3:14])[CH:12]=[CH:11][C:5]2=[N:6][C:7]=1[C@@H:8]([NH2:10])[CH3:9].[NH:15]1[CH2:20][CH2:19][CH2:18][CH:17]([OH:21])[CH2:16]1.CC([O-])(C)C.[K+]>O1CCOCC1>[NH2:10][C@H:8]([C:7]1[N:6]=[C:5]2[CH:11]=[CH:12][N:13]([CH3:14])[C:4]2=[CH:3][C:2]=1[N:15]1[CH2:20][CH2:19][CH2:18][CH:17]([OH:21])[CH2:16]1)[CH3:9]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of (S)-1-(6-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethan-1-amine (508 mg, 2.00 mmol), piperidin-3-ol (1.01 g, 10.0 mmol) and potassium 2-methylpropan-2-olate (1.56 g, 14.0 mmol) in dioxane (15 mL) was heated to 150° C. for 2 hours in a microwave reactor. The solvent was evaporated in vacuo to give the crude product (1.5 g) as a yellow oil which was used in the next step without further purification. ESI-MS m/z [M+H]+ calc'd for C15H22N4O, 275. found 275.

Workup

customThe solvent was evaporated in vacuo

Sources & evidence

ORD record: ord-e541f237a77b477c8cf1df51c972332a
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371321B2

Reaction notes

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