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

HRID 2247700Notes

Reaction equation

HRID 2247700 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:25]O)[S:5][C:6]=1[C:7]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)[O:9][N:8]=1.C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl.[NH:52]1[CH2:55][CH:54]([C:56]([O:58][CH3:59])=[O:57])[CH2:53]1.C(N(CC)C(C)C)(C)C>>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:25][N:52]2[CH2:55][CH:54]([C:56]([O:58][CH3:59])=[O:57])[CH2:53]2)[S:5][C:6]=1[C:7]1[N:11]=[C:10]([C:12]2[CH:13]=[CH:14][C:15]([O:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:16][CH:17]=2)[O:9][N:8]=1

Participants

6

Reactant 5

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 21100040Methyl azetidine-3-carboxylate hydrochlorideHCID 68520727{4-Methyl-5-[5-(4-phenoxyphenyl)-1,2,4-oxadiazol-3-yl]-2-thienyl}methanol

Product 1

HCID 68523708Methyl 1-({4-methyl-5-[5-(4-phenoxyphenyl)-1,2,4-oxadiazol-3-yl]-2-thienyl}methyl)azetidine-3-carboxylate

Procedure

The crude product of the title compound was synthesized by conducting the reaction similar to that mentioned in Example 1 (1f) using {4-methyl-5-[5-(4-phenoxyphenyl)-1,2,4-oxadiazol-3-yl]-2-thienyl}methanol (0.19 g, 0.51 mmol) that was obtained in Example 12 (12a), carbon tetrabromide (0.22 g, 0.66 mmol), triphenylphosphine (0.17 g, 0.66 mmol), methyl 3-azetidinecarboxylate hydrochloride (0.12 g, 0.77 mmol), and N,N-diisopropylethylamine (0.27 mL, 1.5 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 (2:3) as the eluent to afford the title compound (0.20 g) in a yield of 85% as a pale yellowish oily product.

Workup

  1. customthe reaction similar to

Sources & evidence

ORD record
ord-673e6b86f7b84fddb695642be1cc166f
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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