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

HRID 2247713Notes

Reaction equation

HRID 2247713 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:16]2[O:20][N:19]=[C:18]([C:21]3[S:25][C:24]([CH2:26]O)=[CH:23][C:22]=3[CH2:28][CH3:29])[N:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=1.C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl.[NH:55]1[CH2:58][CH:57]([C:59]([O:61][CH3:62])=[O:60])[CH2:56]1.C(N(CC)C(C)C)(C)C>>[Cl:1][C:2]1[CH:3]=[C:4]([C:16]2[O:20][N:19]=[C:18]([C:21]3[S:25][C:24]([CH2:26][N:55]4[CH2:58][CH:57]([C:59]([O:61][CH3:62])=[O:60])[CH2:56]4)=[CH:23][C:22]=3[CH2:28][CH3:29])[N:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=1

Participants

6

Reactant 5

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 21100040Methyl azetidine-3-carboxylate hydrochlorideHCID 68525419(5-{5-[3-Chloro-4-(3-fluorophenoxy)phenyl]-1,2,4-oxadiazol-3-yl}-4-ethyl-2-thienyl)methanol

Product 1

HCID 68523766Methyl 1-[(5-{5-[3-chloro-4-(3-fluorophenoxy)phenyl]-1,2,4-oxadiazol-3-yl}-4-ethyl-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-chloro-4-(3-fluorophenoxy)phenyl]-1,2,4-oxadiazol-3-yl}-4-ethyl-2-thienyl)methanol (0.15 g, 0.34 mmol) that was obtained in Example 16 (16b), carbon tetrabromide (0.16 g, 0.51 mmol), triphenylphosphine (0.13 g, 0.51 mmol), methyl 3-azetidinecarboxylate hydrochloride (0.073 g, 0.51 mmol), and N,N-diisopropylethylamine (0.14 mL, 0.84 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 (2:8 to 5:15) as the eluent to afford the title compound (0.16 g) in a yield of 88% as a colourless oily product.

Workup

  1. customthe reaction similar to

Sources & evidence

ORD record
ord-c8ab182a4d4a48bbadab4ec44f5650d1
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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