2-Methylpyridine-4-boronic acid pinacol ester → 4-(4-Bromo-3,5-dimethyl-phenyl)-2-methyl-pyridine

HRID 237622Notes

Reaction equation

HRID 237622 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:5]=[CH:4][N:3]=1.[Br:17][C:18]1[C:23]([CH3:24])=[CH:22][C:21](I)=[CH:20][C:19]=1[CH3:26]>>[Br:17][C:18]1[C:23]([CH3:24])=[CH:22][C:21]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=2)=[CH:20][C:19]=1[CH3:26]

Participants

3

Reactant 2

HCID 164142742-Methylpyridine-4-boronic acid pinacol esterHCID 207480372-Bromo-5-iodo-1,3-dimethylbenzene

Product 1

HCID 866972944-(4-Bromo-3,5-dimethyl-phenyl)-2-methyl-pyridine

Procedure

The title compound is prepared from 2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine and 2-bromo-5-iodo-1,3-dimethyl-benzene following a procedure analogous to that described in Step 1 of Intermediate 56. LC (method 9): tR=0.87 min; Mass spectrum (ESI+): m/z=276/278 (Br) [M+H]+.

Sources & evidence

ORD record
ord-08a9d603858d48438b97ec8eea88e213
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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