O-BROMOPHENOXYACETIC ACID → HCID 90313995, compound

HRID 1524083Notes

Reaction equation

HRID 1524083 reaction equation
Br[C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7].[F:13][C:14]1[CH:19]=[C:18](B2OC(C)(C)C(C)(C)O2)[CH:17]=[CH:16][C:15]=1[C:29]1[CH:30]=[N:31][C:32]([NH2:35])=[N:33][CH:34]=1>>[NH2:35][C:32]1[N:33]=[CH:34][C:29]([C:15]2[CH:16]=[CH:17][C:18]([C:2]3[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=3[O:4][CH2:5][C:6]([OH:8])=[O:7])=[CH:19][C:14]=2[F:13])=[CH:30][N:31]=1

Participants

3

Reactant 2

HCID 592201O-BROMOPHENOXYACETIC ACIDHCID 903131425-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine

Product 1

HCID 90313995HCID 90313995, compound

Procedure

The title compound was prepared in a manner similar to that described in Example 88 using 2-(2-bromophenoxy)acetic acid and 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine. MS (ESI): mass calcd. for C18H14FN3O3, 339.10; m/z found, 339.9 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 8.46 (d, J=1.4, 2H), 7.71 (d, J=13.3, 1H), 7.51 (d, J=5.7, 2H), 7.29 (dd, J=7.5, 1.7, 1H), 7.25-7.17 (m, 1H), 6.92-6.89 (m, 1H), 6.88-6.80 (m, 3H), 4.14 (s, 2H).

Sources & evidence

ORD record
ord-20315662d3974e19ba4159dc702b3d7f
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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