Carbon tetrabromide → Methyl 1-({5-[5-(4-isobutyl-3-methylphenyl)-1,2,4-oxadiazol-3-yl]pyridin-2-yl}methyl)azetidine-3-carboxylate

HRID 2247774Notes

Reaction equation

HRID 2247774 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:17]=[CH:18][C:19]([CH2:22]O)=[N:20][CH:21]=3)[N:12]=2)=[CH:7][C:6]=1[CH3:24])[CH:2]([CH3:4])[CH3:3].C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl.[NH:50]1[CH2:53][CH:52]([C:54]([O:56][CH3:57])=[O:55])[CH2:51]1.C(N(CC)C(C)C)(C)C>>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:17]=[CH:18][C:19]([CH2:22][N:50]4[CH2:53][CH:52]([C:54]([O:56][CH3:57])=[O:55])[CH2:51]4)=[N:20][CH:21]=3)[N:12]=2)=[CH:7][C:6]=1[CH3:24])[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 5

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 21100040Methyl azetidine-3-carboxylate hydrochlorideHCID 68523492(5-(5-(4-Isobutyl-3-methylphenyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)methanol

Product 1

HCID 68528706Methyl 1-({5-[5-(4-isobutyl-3-methylphenyl)-1,2,4-oxadiazol-3-yl]pyridin-2-yl}methyl)azetidine-3-carboxylate

Procedure

The crude product of the title compound was synthesized by conducting the similar reaction to that mentioned in Example 23 (23g) using {5-[5-(4-isobutyl-3-methylphenyl)-1,2,4-oxadiazol-3-yl]pyridin-2-yl}methanol (0.19 g, 0.58 mmol) that was obtained in Example 28 (28a), carbon tetrabromide (0.39 g, 1.2 mmol), triphenylphosphine (0.30 g, 1.2 mmol), methyl 3-azetidinecarboxylate hydrochloride (0.13 mg, 0.87 mmol), and N,N-diisopropylethylamine (0.30 ml, 1.7 mmol). Subsequently, the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:1 to 2:1 or 3:1) as the eluent to afford the title compound (0.15 g) in a yield of 60% as a white crystalline solid.

Workup

  1. customthe similar reaction to

Sources & evidence

ORD record
ord-bae748b5eac945d5963f9d7ef1b27e1a
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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