Carbon tetrabromide → HCID 68526640, compound

HRID 2247658Notes

Reaction equation

HRID 2247658 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:20]=[C:21]([CH2:24]O)[S:22][CH:23]=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>>[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:20]=[C:21]([CH2:24][N:51]4[CH2:54][CH:53]([C:55]([O:57][CH2:58][CH3:59])=[O:56])[CH2:52]4)[S:22][CH:23]=3)[N:15]=2)=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 44828820Ethyl azetidine-3-carboxylate hydrochlorideHCID 68525625HCID 68525625, compound

Product 1

HCID 68526640HCID 68526640, compound

Procedure

The crude product of the title compound was synthesized by conducting the similar reaction to that mentioned in Example 1 (1f) using {4-[5-(4-benzylphenyl)-1,2,4-oxadiazol-3-yl]-2-thienyl}methanol (95 mg, 0.27 mmol) that was obtained in Example 6 (6a), carbon tetrabromide (0.18 g, 0.54 mmol), triphenylphosphine (0.14 g, 0.54 mmol), ethyl 3-azetidinecarboxylate hydrochloride (67 mg, 0.41 mmol), and N,N-diisopropylethylamine (0.12 ml, 0.68 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 (6:4) as the developing solvent to afford the title compound (84 mg) in a yield of 68% as a white crystalline solid.

Workup

  1. customthe similar reaction to

Sources & evidence

ORD record
ord-632d1c5703f54161834ad69d93063798
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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