Carbon tetrabromide → HCID 68526846, compound

HRID 2247740Notes

Reaction equation

[CH2:1]([C:3]1[CH:7]=[C:6]([C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:15][CH:14]=3)[O:10][N:9]=2)[S:5][C:4]=1[CH2:26]O)[CH3:2].C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl.[NH:53]1[CH2:56][CH:55]([C:57]([O:59][CH3:60])=[O:58])[CH2:54]1.C(N(CC)C(C)C)(C)C>>[CH2:1]([C:3]1[CH:7]=[C:6]([C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:15][CH:14]=3)[O:10][N:9]=2)[S:5][C:4]=1[CH2:26][N:53]1[CH2:56][CH:55]([C:57]([O:59][CH3:60])=[O:58])[CH2:54]1)[CH3:2]

Participants

Reactant 5

HCID 11205Carbon tetrabromide

HCID 11776Triphenylphosphine

HCID 81531Diisopropylethylamine

HCID 21100040Methyl azetidine-3-carboxylate hydrochloride

HCID 68525955HCID 68525955, compound

Product 1

HCID 68526846HCID 68526846, compound

Procedure

The crude product of the title compound was synthesized by conducting the reaction similar to that mentioned in Example 1 (1f) using {3-ethyl-5-[5-(4-phenoxyphenyl)-1,2,4-oxadiazol-3-yl]-2-thienyl}methanol (0.19 g, 0.50 mmol) that was obtained in Example 22 (22f), carbon tetrabromide (0.33 g, 0.99 mmol), triphenylphosphine (0.26 g, 0.99 mmol), methyl 3-azetidinecarboxylate hydrochloride (0.11 g, 0.75 mmol), N,N-diisopropylethylamine (0.22 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 (2:8 to 4:6) as the eluent to afford the title compound (0.17 g) in a yield of 72% as a pale yellow crystalline solid.

Workup

customthe reaction similar to

Sources & evidence

ORD record: ord-04938edecf754837b4e2a68946f2ee8f
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687491B2

Reaction notes

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