2-Amino-5-methylpyridine → HCID 59559933, compound

HRID 1643786Notes

Reaction equation

HRID 1643786 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[Br:9][C:10]1[O:11][C:12]2[C:13](=[C:15]([C:23](OC)=[O:24])[CH:16]=[C:17]([O:19][CH:20]([CH3:22])[CH3:21])[CH:18]=2)[CH:14]=1>>[Br:9][C:10]1[O:11][C:12]2[C:13](=[C:15]([C:23]([NH:1][C:2]3[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=3)=[O:24])[CH:16]=[C:17]([O:19][CH:20]([CH3:22])[CH3:21])[CH:18]=2)[CH:14]=1

Participants

3

Reactant 2

HCID 153482-Amino-5-methylpyridineHCID 59560111HCID 59560111, compound

Product 1

HCID 59559933HCID 59559933, compound

Procedure

The title compound was prepared in a similar manner as described for Example 1, from 2-amino-5-methyl pyridine and methyl 2-bromo-6-isopropoxybenzofuran-4-carboxylate (345a) to give an off-white solid (1.45 g, 53% yield). 1H NMR (400 MHz, CDCl3) δ 8.47 (s, 1 H) 8.27 (d, J=8.31 Hz, 1 H) 8.14 (s, 1 H) 7.60 (dd, J=8.44, 1.89 Hz, 1 H) 7.30 (d, J=2.01 Hz, 1 H) 7.24 (s, 1 H) 7.16 (d, J=1.76 Hz, 1 H) 4.57-4.64 (m, 1 H) 2.34 (s, 3 H) 1.38 (d, J=6.04 Hz, 6 H); LCMS for C18H17BrN2O3m/z 389.00(M+H)+.

Sources & evidence

ORD record
ord-fc652522e29e4d59975a7f9778aafeb3
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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