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

HRID 2247697Notes

Reaction equation

HRID 2247697 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:15]2[O:19][N:18]=[C:17]([C:20]3[S:24][C:23]([CH2:25]O)=[CH:22][C:21]=3[CH3:27])[N:16]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl.[NH:53]1[CH2:56][CH:55]([C:57]([O:59][CH3:60])=[O:58])[CH2:54]1.C(N(CC)C(C)C)(C)C>>[F:1][C:2]1[CH:3]=[C:4]([C:15]2[O:19][N:18]=[C:17]([C:20]3[S:24][C:23]([CH2:25][N:53]4[CH2:56][CH:55]([C:57]([O:59][CH3:60])=[O:58])[CH2:54]4)=[CH:22][C:21]=3[CH3:27])[N:16]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 5

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 21100040Methyl azetidine-3-carboxylate hydrochlorideHCID 68525640{5-[5-(3-Fluoro-4-phenoxyphenyl]-1,2,4-oxadiazol-3-yl)-4-methyl-2-thienyl}methanol

Product 1

HCID 68525875Methyl 1-({5-[5-(3-fluoro-4-phenoxyphenyl)-1,2,4-oxadiazol-3-yl]-4-methyl-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 {5-[5-(3-fluoro-4-phenoxyphenyl]-1,2,4-oxadiazol-3-yl)-4-methyl-2-thienyl}methanol (0.21 g, 0.55 mmol) that was obtained in Example 11 (11f), carbon tetrabromide (0.22 g, 0.66 mmol), triphenylphosphine (0.17 g, 0.66 mmol), methyl 3-azetidinecarboxylate hydrochloride (0.13 g, 0.83 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 using a mixed solvent of ethyl acetate and hexane (5:5) to afford the title compound (0.23 g) in a yield of 86% as a colourless oily product.

Workup

  1. customthe reaction similar to

Sources & evidence

ORD record
ord-b8b377b2fe044d34a53afee444a01c14
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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