3-Aminophenol → HCID 86721809, compound

HRID 1522214Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1I.[NH2:10][C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1.[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:35](Cl)(=[O:38])[CH:36]=[CH2:37]>>[NH2:8][C:4]1[C:3]([C:29]2[CH:30]=[CH:31][C:26]([O:25][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:27][CH:28]=2)=[C:2]([O:17][C:13]2[CH:12]=[C:11]([NH:10][C:35](=[O:38])[CH:36]=[CH2:37])[CH:16]=[CH:15][CH:14]=2)[CH:7]=[CH:6][N:5]=1

Participants

Reactant 4

HCID 115683-Aminophenol

HCID 13140Acryloyl chloride

HCID 27343144-Benzyloxy-phenylboronic acid

HCID 229365964-Chloro-3-iodopyridin-2-amine

Product 1

HCID 86721809HCID 86721809, compound

Procedure

N-(3-((2-amino-3-(4-(benzyloxy)phenyl)pyridin-4-yl)oxy)phenyl)acrylamide was prepared from 4-chloro-3-iodopyridin-2-amine, 3-aminophenol, (4-(benzyloxy)phenyl)boronic acid, and acryloyl chloride using methods A, C, and F. HPLC: 100%. MS: m/z=438 [M+H]+. 1H-NMR (DMSO-D6) δ 10.36 (s, 1H), 7.92 (d, 1H), 7.64 (s, 1H), 7.47-7.32 (m, 11H), 7.16 (d, 2H), 6.86 (m, 1H), 6.40 (dd, 1H), 6.33 (d, 1H), 6.24 (d, 1H), 5.77 (d, 1H), 5.13 (s, 2H).

Sources & evidence

ORD record: ord-a1efb4af066c4621b232550dfe00dfbb
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073947B2

Reaction notes

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