HCID 24692850, compound → HCID 90314362, compound

HRID 1524075Notes

Reaction equation

HRID 1524075 reaction equation
Br[C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][N:6]=1.[F:17][C:18]1[CH:23]=[C:22](B2OC(C)(C)C(C)(C)O2)[CH:21]=[CH:20][C:19]=1[C:33]1[CH:34]=[N:35][C:36]([NH2:39])=[N:37][CH:38]=1>>[NH2:39][C:36]1[N:37]=[CH:38][C:33]([C:19]2[CH:20]=[CH:21][C:22]([C:2]3[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=3[O:4][C:5]3[N:6]=[CH:7][C:8]([C:9]#[N:10])=[CH:11][CH:12]=3)=[CH:23][C:18]=2[F:17])=[CH:34][N:35]=1

Participants

3

Reactant 2

HCID 24692850HCID 24692850, compoundHCID 903131425-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine

Product 1

HCID 90314362HCID 90314362, compound

Procedure

The title compound was prepared in a manner similar to that described in Example 88 using 6-(2-bromophenoxy)nicotinonitrile 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 C22H14FN5O, 383.12; m/z found, 384.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 8.60 (dd, J=2.3, 0.8, 1H), 8.44 (d, J=1.6, 2H), 8.26 (dd, J=8.6, 2.3, 1H), 7.59 (dd, J=7.6, 1.8, 1H), 7.56-7.48 (m, 2H), 7.45-7.39 (m, 1H), 7.36-7.27 (m, 3H), 7.21 (dd, J=8.7, 0.7, 1H), 6.89 (s, 2H).

Sources & evidence

ORD record
ord-09fee7c7612549749b89cbeb4b847f4f
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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