Carbon tetrabromide → HCID 68524364, compound

HRID 2247642Notes

Reaction equation

[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[O:17][N:16]=[C:15]([C:18]4[O:22][C:21]([CH2:23]O)=[CH:20][CH:19]=4)[N:14]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl.[NH:50]1[CH2:53][CH:52]([C:54]([O:56][CH2:57][CH3:58])=[O:55])[CH2:51]1.C(N(CC)C(C)C)(C)C>>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:13]3[O:17][N:16]=[C:15]([C:18]4[O:22][C:21]([CH2:23][N:50]5[CH2:53][CH:52]([C:54]([O:56][CH2:57][CH3:58])=[O:55])[CH2:51]5)=[CH:20][CH:19]=4)[N:14]=3)=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Reactant 5

HCID 11205Carbon tetrabromide

HCID 11776Triphenylphosphine

HCID 81531Diisopropylethylamine

HCID 44828820Ethyl azetidine-3-carboxylate hydrochloride

HCID 68526655HCID 68526655, compound

Product 1

HCID 68524364HCID 68524364, 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-cyclohexylphenyl)-1,2,4-oxadiazol-3-yl]-2-furyl}methanol (0.18 g, 0.55 mmol) that was obtained in Example 2 (2c), carbon tetrabromide (0.22 g, 0.67 mmol), triphenylphosphine (0.18 g, 0.67 mmol), ethyl 3-azetidinecarboxylate hydrochloride (0.14 g, 0.83 mmol) and N,N-diisopropylethylamine (0.30 ml, 1.7 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) as the eluent to afford the title compound (0.23 g) in a yield of 96% as a white crystalline solid.

Workup

customthe similar reaction to

Sources & evidence

ORD record: ord-c2efc98533154663b8279786483c8ca2
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687491B2

Reaction notes

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