3-Aminophenol → HCID 71092823, compound

HRID 1522216Notes

Reaction equation

HRID 1522216 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.[O:18]([C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl.[CH3:35][N:36]([CH3:43])[CH2:37]/[CH:38]=[CH:39]/[C:40](O)=[O:41]>>[NH2:8][C:4]1[C:3]([C:22]2[CH:23]=[CH:24][C:19]([O:18][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:20][CH:21]=2)=[C:2]([O:17][C:13]2[CH:12]=[C:11]([NH:10][C:40](=[O:41])/[CH:39]=[CH:38]/[CH2:37][N:36]([CH3:43])[CH3:35])[CH:16]=[CH:15][CH:14]=2)[CH:7]=[CH:6][N:5]=1

Participants

5

Reactant 4

HCID 115683-AminophenolHCID 27343774-Phenoxyphenylboronic acidHCID 229365964-Chloro-3-iodopyridin-2-amineHCID 45358758(2E)-4-(Dimethylamino)-2-butenoic acid hydrochloride

Product 1

HCID 71092823HCID 71092823, compound

Procedure

(E)-N-(3-((2-amino-3-(4-phenoxyphenyl)pyridin-4-yl)oxy)phenyl)-4-(dimethylamino)but-2-enamide was prepared from 4-chloro-3-iodopyridin-2-amine, 3-aminophenol, (4-phenoxyphenyl)boronic acid, and (E)-4-(dimethylamino)but-2-enoic acid hydrochloride using methods A, C, and E. HPLC: 100%. MS: m/z=481 [M+H]+. 1H-NMR (DMSO-D6) δ 10.51 (s, 1H), 9.88 (broad s, 1H), 7.95 (d, 1H), 7.61 (s, 1H), 7.43-7.32 (m, 8H), 7.17 (t, 1H), 7.12-7.08 (m, 4H), 6.89 (s, 1H), 6.72 (m, 1H), 6.42 (d, 1H), 6.32 (d, 1H), 3.93 (d, 2H), 2.79 (s, 6H).

Sources & evidence

ORD record
ord-2d6df9cc755e4149a2d7307906ab1dc0
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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