Carbon tetrabromide → HCID 68523753, compound

HRID 2247725Notes

Reaction equation

[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]3[S:20][C:19]([CH2:21]O)=[CH:18][C:17]=3[CH2:23][CH3:24])[N:12]=2)=[CH:7][CH:6]=1.C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl.[NH:54]1[CH2:57][CH:56]([C:58]([O:60][CH3:61])=[O:59])[CH2:55]1.C(N(CC)C(C)C)(C)C>>[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]3[S:20][C:19]([CH2:21][N:54]4[CH2:57][CH:56]([C:58]([O:60][CH3:61])=[O:59])[CH2:55]4)=[CH:18][C:17]=3[CH2:23][CH3:24])[N:12]=2)=[CH:7][CH:6]=1

Participants

Reactant 5

HCID 11205Carbon tetrabromide

HCID 11776Triphenylphosphine

HCID 81531Diisopropylethylamine

HCID 21100040Methyl azetidine-3-carboxylate hydrochloride

HCID 68522825HCID 68522825, compound

Product 1

HCID 68523753HCID 68523753, compound

Procedure

The crude product of the title compound was synthesized by conducting the reaction similar to that mentioned in Example 1 (1f) using (5-{5-[4-(2-chlorophenoxy)phenyl]-1,2,4-oxadiazol-3-yl}-4-ethyl-2-thienyl)methanol (0.19 g, 0.46 mmol) that was obtained in Example 19 (19b), carbon tetrabromide (0.18 g, 0.55 mmol), triphenylphosphine (0.14 g, 0.55 mmol), methyl 3-azetidinecarboxylate hydrochloride (0.10 g, 0.69 mmol), and N,N-diisopropylethylamine (0.16 mL, 0.92 mmol). Subsequently, the crude product of the title compound thus obtained was purified by chromatography using a mixed solvent of ethyl acetate and hexane (5:5) to afford the title compound (0.21 g) in a yield of 91% as a pale yellow oily product.

Workup

customthe reaction similar to

Sources & evidence

ORD record: ord-0068c795ad7d47d1a0bab54450cadfde
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687491B2

Reaction notes

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