5-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine → HCID 90312621, compound

HRID 1523886Notes

Reaction equation

HRID 1523886 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([C:11]1[N:15]([CH3:16])[C:14]2[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=2[N:12]=1)(=[O:10])=[O:9].[F:21][C:22]1[CH:27]=[C:26](B2OC(C)(C)C(C)(C)O2)[CH:25]=[CH:24][C:23]=1[C:37]1[CH:38]=[N:39][C:40]([NH2:43])=[N:41][CH:42]=1>>[F:21][C:22]1[CH:27]=[C:26]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8]([C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=3[N:12]=2)(=[O:10])=[O:9])[CH:25]=[CH:24][C:23]=1[C:37]1[CH:42]=[N:41][C:40]([NH2:43])=[N:39][CH:38]=1

Participants

3

Reactant 2

HCID 903131425-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amineHCID 90313983HCID 90313983, compound

Product 1

HCID 90312621HCID 90312621, compound

Procedure

The title compound was prepared in a manner similar to that described in Example 88 using 2-((2-bromophenyl)sulfonyl)-1-methyl-1H-benzo[d]imidazole 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 C24H18FN5O2S, 459.12; m/z found, 460.0 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 7.03-6.96 (dd, J=7.8, 1.5, 1H), 6.88-6.86 (d, J=1.4, 2H), 6.43-6.28 (m, 1.5, 2H), 6.15-6.09 (d, J=8.2, 1H), 6.08-5.99 (m, 2H), 5.97-5.86 (m, 2H), 5.64-5.53 (m, 1H), 5.34-5.30 (dd, J=7.8, 1.7, 1H), 5.30-5.23 (dd, J=11.3, 1.7, 1H), 2.22 (s, 3H).

Sources & evidence

ORD record
ord-8c5ff2da577841ffa4b4ee254012ec6f
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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