Ethyl 3-iodo-4-methylbenzoate → (E)-ethyl 3-(2-(4-methoxy-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)vinyl)-4-methylbenzoate

HRID 2199327Notes

Reaction equation

HRID 2199327 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH:9]=[CH2:10])=[CH:7][N:6]=[C:5]2[N:11]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=[CH:13][C:4]=12.I[C:23]1[CH:24]=[C:25]([CH:31]=[CH:32][C:33]=1[CH3:34])[C:26]([O:28][CH2:29][CH3:30])=[O:27]>>[CH3:1][O:2][C:3]1[C:8](/[CH:9]=[CH:10]/[C:23]2[CH:24]=[C:25]([CH:31]=[CH:32][C:33]=2[CH3:34])[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:7][N:6]=[C:5]2[N:11]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=[CH:13][C:4]=12

Participants

3

Reactant 2

HCID 23073518Ethyl 3-iodo-4-methylbenzoateHCID 673458184-methoxy-1-((2-(trimethylsilyl)ethoxy)methyl)-5-vinyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 68305656(E)-ethyl 3-(2-(4-methoxy-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)vinyl)-4-methylbenzoateYield 58%

Procedure

(E)-ethyl 3-(2-(4-methoxy-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)vinyl)-4-methylbenzoate (302 mg, 58% yield) was prepared as described for Example 5-C starting from 4-methoxy-1-((2-(trimethylsilyl)ethoxy)methyl)-5-vinyl-1H-pyrrolo[2,3-b]pyridine (340 mg, 1.12 mmol) and ethyl 3-iodo-4-methylbenzoate (360 mg, 1.24 mmol). 1H NMR (600 MHz, CDCl3) δ 8.52 (s, 1H), 8.35 (d, J=1.2 Hz, 1H), 7.87 (dd, J=1.8, 7.8 Hz, 1H), 7.45 (d, J=16.2 Hz, 1H), 7.34 (d, J=16.2 Hz, 1H), 7.31-7.27 (m, 2H), 6.81 (d, J=3.6 Hz, 1H), 5.71 (s, 2H), 4.45 (q, J=7.2 Hz, 2H), 4.43 (s, 3H), 3.62 (t, J=8.4 Hz, 2H), 2.51 (s, 3H), 1.46 (t, J=7.2 Hz, 3H), 0.97 (t, J=8.4 Hz, 2H), 0 (s, 9H). MS m/z: 467 [M+1].

Sources & evidence

ORD record
ord-f428dc8e638d45e1843fe304aa71606b
Source dataset
uspto-grants-2016_06
Patent number
US09358231B2

Reaction notes

Loading…