Trimethylsilylacetylene → (3-Methyl-5-trimethylsilanylethynyl-pyridin-2-yl)-(2-pyrrolidin-1-yl-ethyl)-amine

HRID 1916746Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH3:16])[C:5]([NH:8][CH2:9][CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:6][CH:7]=1.[C:17]([Si:19]([CH3:22])([CH3:21])[CH3:20])#[CH:18]>>[CH3:16][C:4]1[C:5]([NH:8][CH2:9][CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:6][CH:7]=[C:2]([C:18]#[C:17][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH:3]=1

Participants

Reactant 2

HCID 66111Trimethylsilylacetylene

HCID 67363857(5-Bromo-3-methyl-pyridin-2-yl)-(2-pyrrolidin-1-yl-ethyl)-amine

Product 1

HCID 67363503(3-Methyl-5-trimethylsilanylethynyl-pyridin-2-yl)-(2-pyrrolidin-1-yl-ethyl)-amine

Conditions

Temperature: 50 °C

Procedure

Prepared analogously to Example 15c from 500 mg (1.76 mmol) (5-bromo-3-methyl-pyridin-2-yl)-(2-pyrrolidin-1-yl-ethyl)-amine and 0.29 mL (2.11 mmol) ethynyl-trimethyl-silane, while the reaction mixture is heated to 50° C. for 12 h.

Sources & evidence

ORD record: ord-dfa572912b6a4c0eac467c3e378a6dca
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618132B2

Reaction notes

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