Methyl 3-(2-bromoethoxy)benzoate → 3-[2-(5-Cyano-3-methyl-2-pyridin-3-yl-indol-1-yl)-ethoxy]-benzoic acid methyl ester

HRID 1661580Notes

Reaction equation

HRID 1661580 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][CH2:12]Br)[CH:5]=1.[CH3:15][C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:25]#[N:26])[CH:23]=2)[NH:18][C:17]=1[C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1>>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][CH2:12][N:18]2[C:19]3[C:24](=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=3)[C:16]([CH3:15])=[C:17]2[C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)[CH:5]=1

Participants

3

Reactant 2

HCID 10491483Methyl 3-(2-bromoethoxy)benzoateHCID 445541323-methyl-2-pyridin-3-yl-1H-indole-5-carbonitrile

Product 1

HCID 582157453-[2-(5-Cyano-3-methyl-2-pyridin-3-yl-indol-1-yl)-ethoxy]-benzoic acid methyl ester

Procedure

3-(2-Bromo-ethoxy)-benzoic acid methyl ester and 5-cyano-3-methyl-2-pyridin-3-yl-indol-1-yl (Example 6) are processed according to the method described in Example 59 to give 3-[2-(5-cyano-3-methyl-2-pyridin-3-yl-indol-1-yl)-ethoxy]-benzoic acid methyl ester. 1H NMR (400 MHz, MeOD) δ ppm 2.26 (s, 3H), 3.90 (s, 3H), 4.22 (t, J=4.9 Hz, 2H), 4.60 (t, J=5.1 Hz, 2H), 6.91 (dd, J=7.8, 2.3 Hz, 1H), 7.21-7.24 (m, 1H), 7.28 (t, J=8.0 Hz, 1H), 7.52-7.59 (m, 2H), 7.65 (dd, J=7.8, 5.1 Hz, 1H), 7.76 (d, J=8.6 Hz, 1H), 7.98-8.09 (m, 2H), 8.56-8.77 (m, 2H). HRMS (ESI) m/z 412.1664 [(M+H)+ Calcd for C25H22N3O3: 412.1661].

Sources & evidence

ORD record
ord-c60b51b55dd94026a3f7d61fcc246ba3
Source dataset
uspto-grants-2011_10
Patent number
US08030334B2

Reaction notes

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