tert-Butyl (5-ethynylpyridin-2-yl)carbamate → HCID 58362386, compound

HRID 2361479Notes

Reaction equation

HRID 2361479 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[N:7][CH:8]=1)#[CH:2].Br[C:18]1[N:22]([CH2:23][CH2:24][F:25])[C:21]2[CH:26]=[CH:27][CH:28]=[CH:29][C:20]=2[N:19]=1>>[F:25][CH2:24][CH2:23][N:22]1[C:21]2[CH:26]=[CH:27][CH:28]=[CH:29][C:20]=2[N:19]=[C:18]1[C:2]#[C:1][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[N:7][CH:8]=1

Participants

3

Reactant 2

HCID 58362538tert-Butyl (5-ethynylpyridin-2-yl)carbamateHCID 58362709HCID 58362709, compound

Product 1

HCID 58362386HCID 58362386, compoundYield 31.5%

Procedure

tert-Butyl (5-ethynylpyridin-2-yl)carbamate (22 mg, 0.1 mmol) and 2-bromo-1-(2-fluoroethyl)-1H-benzo[d]imidazole (24.3 mg, 0.1 mmol) was reacted using general procedure B to afford tert-butyl (5-((1-(2-fluoroethyl)-1H-benzo[d]imidazol-2-yl)ethynyl)pyridin-2-yl)carbamate (12 mg, 31%). 1H NMR (300 MHz, CDCl3): 8.51 (d, J=1.6 Hz, 1H), 8.47 (m, 1H), 7.88 (dd, J=8.8, 2.4 Hz, 7.40-7.34 (m, 3H), 7.31 (d, J=12.8 Hz, 6.22 (s, 1H), 4.80 (t, J=4.8 Hz, 1H), 4.68 (t, J=4.8 Hz, 1H), 4.53 (m, 1H), 4.47 (m, 1H), 1.55 (s, 9H).

Sources & evidence

ORD record
ord-2f120dc865194db2b7850edc5ad8c73e
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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