Carbon tetrabromide → Methyl 1-({5-[5-(3-chloro-4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-6-ethylpyridin-2-yl}methyl)azetidine-3-carboxylate

HRID 2247762Notes

Reaction equation

HRID 2247762 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][C:20]([CH2:25]O)=[N:21][C:22]=3[CH2:23][CH3:24])[N:13]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]([CH3:11])[CH3:10].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>>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][C:20]([CH2:25][N:52]4[CH2:55][CH:54]([C:56]([O:58][CH3:59])=[O:57])[CH2:53]4)=[N:21][C:22]=3[CH2:23][CH3:24])[N:13]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]([CH3:11])[CH3:10]

Participants

6

Reactant 5

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 21100040Methyl azetidine-3-carboxylate hydrochlorideHCID 68521068{5-[5-(3-Chloro-4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-6-ethylpyridin-2-yl}methanol

Product 1

HCID 68524350Methyl 1-({5-[5-(3-chloro-4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-6-ethylpyridin-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-(3-chloro-4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-6-ethylpyridin-2-yl}methanol (0.15 g, 0.40 mmol) that was obtained in Example 25 (25c), carbon tetrabromide (0.27 g, 0.80 mmol), triphenylphosphine (0.21 g, 0.80 mmol), methyl 3-azetidinecarboxylate hydrochloride (91 mg, 0.60 mmol) and N,N-diisopropylethylamine (0.21 ml, 1.2 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 (0.16 g) in a yield of 83% as a pale yellowish oily product.

Workup

  1. customthe similar reaction to

Sources & evidence

ORD record
ord-15bf9bb01f144fc2895ef014ce3b973a
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

Loading…