Carbon tetrabromide → HCID 68523928, compound

HRID 2247729Notes

Reaction equation

[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:28]O)[S:6][C:7]=1[C:8]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=3)=[C:15]([F:27])[CH:14]=2)[O:10][N:9]=1)[CH3:2].C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl.[NH:55]1[CH2:58][CH:57]([C:59]([O:61][CH3:62])=[O:60])[CH2:56]1.C(N(CC)C(C)C)(C)C>>[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:28][N:55]2[CH2:58][CH:57]([C:59]([O:61][CH3:62])=[O:60])[CH2:56]2)[S:6][C:7]=1[C:8]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=3)=[C:15]([F:27])[CH:14]=2)[O:10][N:9]=1)[CH3:2]

Participants

Reactant 5

HCID 11205Carbon tetrabromide

HCID 11776Triphenylphosphine

HCID 81531Diisopropylethylamine

HCID 21100040Methyl azetidine-3-carboxylate hydrochloride

HCID 68525865HCID 68525865, compound

Product 1

HCID 68523928HCID 68523928, compound

Procedure

The crude product of the title compound was synthesized by conducting the reaction similar to that mentioned in Example 1 (1f) using (4-ethyl-5-{5-[3-fluoro-4-(3-fluorophenoxy)phenyl]-1,2,4-oxadiazol-3-yl}-2-thienyl)methanol (0.18 g, 0.43 mmol) that was obtained in Example 20 (20b), carbon tetrabromide (0.22 g, 0.65 mmol), triphenylphosphine (0.17 g, 0.65 mmol), methyl 3-azetidinecarboxylate hydrochloride (99 mg, 0.65 mmol), N,N-diisopropylethylamine (0.22 mL, 1.3 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 (1:3 to 1:2) as the eluent to afford the title compound (0.14 g) in a yield of 64% as a pale yellow oily product.

Workup

customthe reaction similar to

Sources & evidence

ORD record: ord-cf7567cde00e47808d091e9db062aea7
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687491B2

Reaction notes

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