1-methyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazole-5-carbaldehyde → 6-Chloro-2-(2-(1-methyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazol-5-yl)vinyl)-[1,2,4]triazolo[1,5-a]pyridine

HRID 1054965Notes

Reaction equation

HRID 1054965 reaction equation
[Cl-].[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]([N:9]=[C:10]([CH2:12][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:11]=2)[CH:8]=1.[CH3:32][N:33]1[C:37]([CH:38]=O)=[N:36][C:35]([N:40]2[CH2:44][CH2:43][CH2:42][CH2:41]2)=[N:34]1>>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]([N:9]=[C:10]([CH:12]=[CH:38][C:37]3[N:33]([CH3:32])[N:34]=[C:35]([N:40]4[CH2:44][CH2:43][CH2:42][CH2:41]4)[N:36]=3)[N:11]=2)[CH:8]=1

Participants

3

Reactant 2

HCID 838754401-methyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazole-5-carbaldehydeHCID 90025615((6-Chloro-[1,2,4]triazolo[1,5-a]pyridin-2-yl)methyl)triphenylphosphonium chloride

Product 1

HCID 1235482036-Chloro-2-(2-(1-methyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazol-5-yl)vinyl)-[1,2,4]triazolo[1,5-a]pyridineYield 91.1%

Procedure

The desired product was prepared in analogy to Example 1 g) from ((6-chloro-[1,2,4]triazolo[1,5-a]pyridin-2-yl)methyl)triphenylphosphonium chloride (170 mg, 366 μmol, Eq: 1.00) and 1-methyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazole-5-carbaldehyde (66.0 mg, 366 μmol, Eq: 1.00). 110 mg (91%) of the desired product were obtained as a light yellow solid. MS: m/z=330.4 (M+H+)

Sources & evidence

ORD record
ord-f5f10c85a67347a795b7220f91093d2a
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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