Tetrahydrofuran → HCID 66734230, compound

HRID 1929704Notes

Reaction equation

HRID 1929704 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH2:18][CH3:19])=[N:15][C:16](I)=[C:10]2[CH:9]1[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[C:24]([Cl:32])[CH:23]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Mg]Br)C.C1COCC1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH2:18][CH3:19])=[N:15][CH:16]=[C:10]2[CH:9]1[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:30])([F:31])[F:29])=[C:24]([Cl:32])[CH:23]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 66734285HCID 66734285, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 66734230HCID 66734230, compoundYield 72.1%

Procedure

According to the previously described general procedure (GP12C), treatment of 8-[2-(3-chloro-4-trifluoromethyl-phenyl)-ethyl]-3-ethyl-1-iodo-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester (2.070 g; 3.546 mmol) with 1M ethylmagnesium bromide in THF (15.6 ml; 15.6 mmol; 4.4 eq.) afforded 8-[2-(3-chloro-4-trifluoromethyl-phenyl)-ethyl]-3-ethyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester (1.170 g; 72%) as a pale yellow oil. LC-MS: tR=0.95 min.; [M+H]+=457.98 g/mol.

Sources & evidence

ORD record
ord-dd8651af58524fa6a704ab13b1a73681
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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