Methyl iodide → HCID 59320816, compound

HRID 341251Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]([CH3:9])[N:5]([CH3:8])[C:6]=1[CH3:7].BrC1N(C)C(C)=C(Br)N=1.C([Li])CCC.CI.CC1(C)C(C)(C)OB([C:34]2[CH:39]=[CH:38][N:37]3[C:40]([C:43]4[CH:44]=[C:45]([NH:49][C:50]([NH:52][CH2:53][C:54]([F:57])([F:56])[F:55])=[O:51])[CH:46]=[CH:47][CH:48]=4)=[CH:41][N:42]=[C:36]3[CH:35]=2)O1>>[F:57][C:54]([F:56])([F:55])[CH2:53][NH:52][C:50]([NH:49][C:45]1[CH:46]=[CH:47][CH:48]=[C:43]([C:40]2[N:37]3[CH:38]=[CH:39][C:34]([C:2]4[N:3]=[C:4]([CH3:9])[N:5]([CH3:8])[C:6]=4[CH3:7])=[CH:35][C:36]3=[N:42][CH:41]=2)[CH:44]=1)=[O:51]

Participants

Reactant 5

HCID 6328Methyl iodide

HCID 72048732,4-Dibromo-1,5-dimethyl-1H-imidazole

HCID 300329971036990-53-0

HCID 59320805HCID 59320805, compound

HCID 178418339Butyllithium

Product 1

HCID 59320816HCID 59320816, compound

Procedure

4-Bromo-1,2,5-trimethyl-1H-imidazole may be prepared from 2,4-dibromo-1,5-dimethyl-1H-imidazole by treatment with n-butyl lithium and methyl iodide as described in J. Org. Chem., 1994, 59, 5524. This may be coupled with 1-[3-(7-boronic acid-imidazo[1,2-a]pyridin-3-yl)-phenyl]-3-(2,2,2-trifluoro-ethyl)-urea or 1-{3-[7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-imidazo[1,2-a]pyridin-3-yl]-phenyl}-3-(2,2,2-trifluoro-ethyl)-urea according to procedure E3.

Sources & evidence

ORD record: ord-015b6e61ce1a45b6a3f2a9eb39f45ffd
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895745B2

Reaction notes

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