1-Methyl-1H-indole-5-boronic acid → HCID 69297579, compound

HRID 1930362Notes

Reaction equation

HRID 1930362 reaction equation
[C:1]([C:5]1[N:10]=[C:9](Cl)[C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:16][N:17]1[C:25]2[C:20](=[CH:21][C:22](B(O)O)=[CH:23][CH:24]=2)[CH:19]=[CH:18]1>>[C:1]([C:5]1[N:10]=[C:9]([C:22]2[CH:21]=[C:20]3[C:25](=[CH:24][CH:23]=2)[N:17]([CH3:16])[CH:18]=[CH:19]3)[C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 27598671-Methyl-1H-indole-5-boronic acidHCID 77134375HCID 77134375, compound

Product 1

HCID 69297579HCID 69297579, compoundYield 74.8%

Procedure

Using a procedure analogous to Example B32, methyl 2-tert-butyl-4-chloropyrimidine-5-carboxylate (0.849 g, 3.71 mmol), N-methylindole-5-boronic acid (1.30 g, 7.43 mmol) and tetrakis-(triphenylphosphine)palladium(0) (86 mg) were combined to give methyl 2-tert-butyl-4-(1-methyl-1 H-indol-5-yl)pyrimidine-5-carboxylate (898 mg, 74% yield). 1H NMR (300 MHz, DMSO-d6): δ 1.40 (s, 9 H), 3.70 (s, 3 H), 3.82 (s, 3 H), 6.57 (s, 1 H), 7.41-7.44 (m, 2 H), 7.53 (d, J=8.6 Hz, 1 H), 7.92 (s, 1 H), 8.94 (s, 1 H); MS (ESI) m/z: 324.0 (M+H+).

Sources & evidence

ORD record
ord-3455e61752004433923440cc6bef70fc
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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