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

HRID 2247780Notes

Reaction equation

HRID 2247780 reaction equation
[CH2:1]([C:3]1[N:8]=[C:7]([CH2:9]O)[CH:6]=[CH:5][C:4]=1[C:11]1[N:15]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([CH3:25])[CH3:24])=[C:18]([F:26])[CH:17]=2)[O:13][N:12]=1)[CH3:2].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>>[CH2:1]([C:3]1[N:8]=[C:7]([CH2:9][N:52]2[CH2:55][CH:54]([C:56]([O:58][CH3:59])=[O:57])[CH2:53]2)[CH:6]=[CH:5][C:4]=1[C:11]1[N:15]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([CH3:25])[CH3:24])=[C:18]([F:26])[CH:17]=2)[O:13][N:12]=1)[CH3:2]

Participants

6

Reactant 5

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 21100040Methyl azetidine-3-carboxylate hydrochlorideHCID 68522114{6-Ethyl-5-[5-(3-fluoro-4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]pyridin-2-yl}methanol

Product 1

HCID 68521697Methyl 1-({6-ethyl-5-[5-(3-fluoro-4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]pyridin-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 {6-ethyl-5-[5-(3-fluoro-4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]pyridin-2-yl}methanol (0.13 g, 0.38 mmol) that was obtained in Example 30 (30a), carbon tetrabromide (0.25 g, 0.75 mmol), triphenylphosphine (0.20 g, 0.75 mmol), methyl 3-azetidinecarboxylate hydrochloride (78 mg, 0.51 mmol), and N,N-diisopropylethylamine (0.15 ml, 0.86 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 (3:7 to 7:3) as the eluent to afford the title compound (0.11 g) in a yield of 69% as a pale yellow oily product.

Workup

  1. customthe similar reaction to

Sources & evidence

ORD record
ord-591a9b731ddc4a84bfe7644295c484e0
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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