(2-Methoxypyridin-4-yl)boronic acid → N-(1-(6-amino-2'-methoxy-[3,4'-bipyridin]-2-yl)-2-(3,5-difluorophenyl)ethyl)-2-(5-fluoro-1H-indol-3-yl)acetamide

HRID 2170317

Reaction equation

HRID 2170317 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C@@H:8]([NH:18][C:19](=[O:31])[CH2:20][C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([F:30])[CH:28]=3)[NH:23][CH:22]=2)[CH2:9][C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=2)[C:5]([C:32]2[CH:33]=CC(F)=[C:36]([CH:40]=2)C(N)=O)=[CH:4][CH:3]=1.NC1N=C(C(NC(=O)CC2C3C(=CC=C(F)C=3)NC=2)CC2C=C(F)C=C(F)C=2)C(Br)=CC=1.[CH3:74][O:75][C:76]1C=C(B(O)O)C=C[N:77]=1>>[NH2:1][C:2]1[N:7]=[C:6]([CH:8]([NH:18][C:19](=[O:31])[CH2:20][C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([F:30])[CH:28]=3)[NH:23][CH:22]=2)[CH2:9][C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=2)[C:5]([C:32]2[CH:40]=[CH:36][N:77]=[C:76]([O:75][CH3:74])[CH:33]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 23546919(2-Methoxypyridin-4-yl)boronic acidHCID 90281232N-(1-(6-amino-3-bromopyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)-2-(5-fluoro-1H-indol-3-yl)acetamideHCID 90281459(S)-5-(6-amino-2-(2-(3,5-difluorophenyl)-1-(2-(5-fluoro-1H-indol-3-yl)acetamido)ethyl)pyridin-3-yl)-2-fluorobenzamide

Product 1

HCID 90281345N-(1-(6-amino-2'-methoxy-[3,4'-bipyridin]-2-yl)-2-(3,5-difluorophenyl)ethyl)-2-(5-fluoro-1H-indol-3-yl)acetamide

Procedure

The title compound was prepared according to the method presented for the synthesis of compound 1H of Example 1 utilizing 1G and (2-methoxypyridin-4-yl)boronic acid. 1H NMR (400 MHz, DMSO) δ 10.89 (s, 1H), 7.96 (d, J=5.2 Hz, 1H), 7.25 (dd, J=8.9, 4.3 Hz, 2H), 7.14-7.10 (m, 3H), 6.88-6.80 (m, 3H), 6.67 (d, J=5.2 Hz, 1H), 6.45-6.38 (m, 5H), 5.00 (d, J=7.3 Hz, 1H), 3.75 (s, 2H), 2.89 (m, 2H). MS (m/z) 532.4 [M+H]+.

Sources & evidence

ORD record
ord-54c318af6c014eb182b91e034d4a8141
Source dataset
uspto-grants-2015_06
Patent number
US09050344B2

Linked notes

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