Carbon tetrabromide → HCID 68523376, compound

HRID 2247655Notes

Reaction equation

[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:18][N:17]=[C:16]([C:19]3[S:23][C:22]([CH2:24]O)=[CH:21][CH:20]=3)[N:15]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl.[NH:51]1[CH2:54][CH:53]([C:55]([O:57][CH2:58][CH3:59])=[O:56])[CH2:52]1.C(N(CC)C(C)C)(C)C>>[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:18][N:17]=[C:16]([C:19]3[S:23][C:22]([CH2:24][N:51]4[CH2:54][CH:53]([C:55]([O:57][CH2:58][CH3:59])=[O:56])[CH2:52]4)=[CH:21][CH:20]=3)[N:15]=2)=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 5

HCID 11205Carbon tetrabromide

HCID 11776Triphenylphosphine

HCID 81531Diisopropylethylamine

HCID 44828820Ethyl azetidine-3-carboxylate hydrochloride

HCID 68523477HCID 68523477, compound

Product 1

HCID 68523376HCID 68523376, compound

Procedure

The crude product of the title compound was synthesized by conducting the similar reaction to that mentioned in Example 1 (1f) using {5-[5-(4-phenoxyphenyl)-1,2,4-oxadiazol-3-yl]-2-thienyl}methanol (97 m g, 0.28 mmol) that was obtained in Example 5 (5a), carbon tetrabromide (0.19 g, 0.56 mmol), triphenylphosphine (0.15 g, 0.56 mmol), ethyl 3-azetidinecarboxylate hydrochloride (70 mg, 0.42 mmol), and N,N-diisopropylethylamine (0.18 ml, 1.1 mmol). Subsequently, the crude product of the title compound thus obtained was purified by thin layer chromatography on a silica gel plate using a mixed solvent of ethyl acetate and hexane (4:3) as the developing solvent to afford the title compound (93 mg) in a yield of 72% as a colourless oily product.

Workup

customthe similar reaction to

Sources & evidence

ORD record: ord-4953181d75a54052867b503894f4ee60
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687491B2

Reaction notes

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