HCID 68573076, compound → HCID 71092861, compound

HRID 1522305Notes

Reaction equation

HRID 1522305 reaction equation
I[C:2]1[C:3]([NH2:22])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:11][CH:10]=1.CC1(C)C(C)(C)OB([C:31]2[CH:32]=[C:33]([NH:37][C:38](=[O:41])[CH2:39][CH3:40])[CH:34]=[CH:35][CH:36]=2)O1>>[NH2:22][C:3]1[C:2]([C:35]2[CH:34]=[C:33]([NH:37][C:38](=[O:41])[CH2:39][CH3:40])[CH:32]=[CH:31][CH:36]=2)=[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:11][CH:10]=2)[CH:6]=[CH:5][N:4]=1

Participants

3

Reactant 2

HCID 68573076HCID 68573076, compoundHCID 71092832HCID 71092832, compound

Product 1

HCID 71092861HCID 71092861, compoundYield 49%

Procedure

N-(3-(2-amino-4-(4-phenoxyphenoxy)pyridin-3-yl)phenyl)propionamide was prepared from 3-iodo-4-(4-phenoxyphenoxy)pyridin-2-amine and N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propionamide using Method C (49% yield). HPLC: 98%, RT=4.186 min. MS: m/z=426 [M+H]+, RT=4.18 min. 1H-NMR (DMSO-d6) δ 10.01 (s, 1H), 7.94 (d, 1H), 7.73 (s, 1H), 7.63 (d, 1H), 7.44 (t, 1H), 7.39 (t, 2H), 7.24 (s, 2H), 7.16-7.01 (m, 8H), 6.35 (d, 1H), 2.32 (q, 2H), 1.07 (t, 3H).

Sources & evidence

ORD record
ord-b4d83f2e61064202be179cf4890ae992
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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