HCID 64589951, compound → HCID 90313978, compound

HRID 1524071Notes

Reaction equation

HRID 1524071 reaction equation
Br[C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][C:5]1[N:10]=[C:9]([C:11]#[N:12])[CH:8]=[CH:7][CH: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:10]=[C:9]([C:11]#[N:12])[CH:8]=[CH:7][CH:6]=3)=[CH:23][C:18]=2[F:17])=[CH:34][N:35]=1

Participants

3

Reactant 2

HCID 64589951HCID 64589951, compoundHCID 903131425-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine

Product 1

HCID 90313978HCID 90313978, compound

Procedure

The title compound was prepared in a manner similar to that described in Example 88 using 6-(2-bromophenoxy)picolinonitrile 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, 383.9 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 8.40 (d, J=1.4, 2H), 7.99 (dd, J=8.5, 7.4, 1H), 7.71-7.67 (m, 1H), 7.56 (dd, J=7.6, 1.7, 1H), 7.55-7.46 (m, 2H), 7.42-7.37 (m, 1H), 7.35-7.25 (m, 4H), 6.85 (s, 2H).

Sources & evidence

ORD record
ord-dbc7701ed3b549378aeab3b9d3ee513d
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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