1-ethyl-1H-pyrazole-3-carbaldehyde → HCID 68294498, compound

HRID 715059Notes

Reaction equation

HRID 715059 reaction equation
O1[C:5]([CH:6]=O)=[CH:4][N:3]=[CH:2]1.[CH3:8][N:9]1[CH:13]=[CH:12][C:11](C=O)=[N:10]1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([Mg]Br)=[CH:19][C:18]=1[F:25].[CH2:26]([N:28]1C=CC(C=O)=[N:29]1)[CH3:27]>>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([N:3]([C:11]2[CH:12]=[CH:13][N:9]([CH3:8])[N:10]=2)[CH3:2])=[CH:19][C:18]=1[F:25].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([N:3]([C:4]2[CH:5]=[CH:6][N:28]([CH2:26][CH3:27])[N:29]=2)[CH3:2])=[CH:19][C:18]=1[F:25]

Participants

6

Reactant 4

HCID 70194151-ethyl-1H-pyrazole-3-carbaldehydeHCID 70260901-Methyl-1H-pyrazole-3-carboxaldehydeHCID 118293725-OXAZOLECARBOXALDEHYDE2×HCID 178505943HCID 178505943, compound

Product 2

HCID 68294498HCID 68294498, compoundHCID 117965526HCID 117965526, compound

Procedure

(4-Chloro-3-fluoro-phenyl)-(1-methyl-1H-pyrazol-3-yl)-methylamine (32a) was prepared analogously except oxazole-5-carbaldehyde was replaced with 1-methyl-1H-pyrazole-3-carbaldehyde (CASRN 27258-32-8) and (4-chloro-3-fluorophenyl)magnesium bromide was used in place of (3,4-dichlorophenyl)magnesium bromide in step 2. (4-Chloro-3-fluoro-phenyl)-(1-ethyl-1H-pyrazol-3-yl)-methylamine (32b) was prepared analogously except oxazole-5-carbaldehyde was replaced with 1-ethyl-1H-pyrazole-3-carbaldehyde (CASRN 942319-16-6).

Sources & evidence

ORD record
ord-4cdeb1143bcb4dc8a28386fc7ee1c42c
Source dataset
uspto-grants-2015_11
Patent number
US09187462B2

Reaction notes

Loading…