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

HRID 2247717Notes

Reaction equation

HRID 2247717 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:27]O)[S:6][C:7]=1[C:8]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=3)=[CH:15][CH:14]=2)[O:10][N:9]=1)[CH3:2].C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl.[NH:54]1[CH2:57][CH:56]([C:58]([O:60][CH3:61])=[O:59])[CH2:55]1.C(N(CC)C(C)C)(C)C>>[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:27][N:54]2[CH2:57][CH:56]([C:58]([O:60][CH3:61])=[O:59])[CH2:55]2)[S:6][C:7]=1[C:8]1[N:12]=[C:11]([C:13]2[CH:14]=[CH:15][C:16]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=3)=[CH:17][CH:18]=2)[O:10][N:9]=1)[CH3:2]

Participants

6

Reactant 5

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 21100040Methyl azetidine-3-carboxylate hydrochlorideHCID 68524722(4-Ethyl-5-{5-[4-(3-fluorophenoxy)phenyl]-1,2,4-oxadiazol-3-yl}-2-thienyl)methanol

Product 1

HCID 68525784Methyl 1-[(4-ethyl-5-{5-[4-(3-fluorophenoxy)phenyl]-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-ethyl-5-{5-[4-(3-fluorophenoxy)phenyl]-1,2,4-oxadiazol-3-yl}-2-thienyl)methanol (0.15 g, 0.38 mmol) that was obtained in Example 17 (17b), carbon tetrabromide (0.15 g, 0.45 mmol), triphenylphosphine (0.12 g, 0.45 mmol), methyl 3-azetidinecarboxylate hydrochloride (86 mg, 0.57 mmol), and N,N-diisopropylethylamine (0.19 mL, 1.1 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 (0.16 g) in a yield of 85% as a pale yellow oily product.

Workup

  1. customthe reaction similar to

Sources & evidence

ORD record
ord-9a0ff45e190f465ca6714a1c088988f9
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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