Carbon tetrabromide → HCID 68525948, compound

HRID 2247652Notes

Reaction equation

[C:1]1([C:7]2[CH:8]=[C:9]([C:16]3[O:20][N:19]=[C:18]([C:21]4[S:25][C:24]([CH2:26]O)=[CH:23][CH:22]=4)[N:17]=3)[S:10][C:11]=2[C:12]([F:15])([F:14])[F:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.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][CH2:60][CH3:61])=[O:58])[CH2:54]1.C(N(CC)C(C)C)(C)C>>[C:1]1([C:7]2[CH:8]=[C:9]([C:16]3[O:20][N:19]=[C:18]([C:21]4[S:25][C:24]([CH2:26][N:53]5[CH2:56][CH:55]([C:57]([O:59][CH2:60][CH3:61])=[O:58])[CH2:54]5)=[CH:23][CH:22]=4)[N:17]=3)[S:10][C:11]=2[C:12]([F:15])([F:14])[F:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Reactant 5

HCID 11205Carbon tetrabromide

HCID 11776Triphenylphosphine

HCID 81531Diisopropylethylamine

HCID 44828820Ethyl azetidine-3-carboxylate hydrochloride

HCID 68522049(5-{5-[4-Phenyl-5-(trifluoromethyl)-2-thienyl]-1,2,4-oxadiazol-3-yl}-2-thienyl)methanol

Product 1

HCID 68525948HCID 68525948, 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-phenyl-5-(trifluoromethyl)-2-thienyl]-1,2,4-oxadiazol-3-yl}-2-thienyl)methanol (0.12 g, 0.29 mmol) that was obtained in Example 4 (4c), carbon tetrabromide (0.19 g, 0.58 mmol), triphenylphosphine (0.15 g, 0.58 mmol), ethyl 3-azetidinecarboxylate hydrochloride (62 mg, 0.38 mmol), and N,N-diisopropylethylamine (0.13 ml, 0.73 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 (4:5) as the developing solvent to afford the title compound (0.12 g) in a yield of 80% as a colourless oily product.

Workup

customthe similar reaction to

Sources & evidence

ORD record: ord-28b92075f6e9421d80dbcd4e02eac1b8
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687491B2

Reaction notes

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