3,5-Dimethylisoxazole-4-boronic acid pinacol ester → HCID 24962502, compound

HRID 383902Notes

Reaction equation

[CH3:1][C:2]1[C:6](B2OC(C)(C)C(C)(C)O2)=[C:5]([CH3:16])[O:4][N:3]=1.[CH2:17]([C:20]1([CH3:44])[C:29]2[C:24](=[C:25]3[CH2:33][CH2:32][CH2:31][C:26]3=[C:27](Br)[CH:28]=2)[N:23](C(OC(C)(C)C)=O)[C:22]([CH3:42])([CH3:41])[C:21]1=[O:43])[CH:18]=[CH2:19].ClC1C=C(O)C=CC=1C1C=C2C(=C3CCCC=13)NC(C)(C)C(=O)C2(C)C>>[CH2:17]([C:20]1([CH3:44])[C:29]2[C:24](=[C:25]3[CH2:33][CH2:32][CH2:31][C:26]3=[C:27]([C:6]3[C:2]([CH3:1])=[N:3][O:4][C:5]=3[CH3:16])[CH:28]=2)[NH:23][C:22]([CH3:42])([CH3:41])[C:21]1=[O:43])[CH:18]=[CH2:19]

Participants

Reactant 3

HCID 27586563,5-Dimethylisoxazole-4-boronic acid pinacol ester

HCID 24961054HCID 24961054, compound

HCID 68558441HCID 68558441, compound

Product 1

HCID 24962502HCID 24962502, compoundYield 31%

Procedure

Using 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole instead of tert-butyl 2,2,4,4-tetramethyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3,4,7,8,9-hexahydro-1H-cyclopenta[h]quinolin-3-one-1-carboxylate of Example 1, 10), using tert-butyl 4-allyl-6-bromo-2,2,4-trimethyl-2,3,4,7,8,9-hexahydro-1H-cyclopenta[h]quinolin-3-one-1-carboxylate obtained in Example 50, 1) instead of 4-bromo-3-chlorophenol of Example 1, 10) and according to a similar method, the title compound (25 mg, 31%) was obtained.

Sources & evidence

ORD record: ord-cbb93898954140bcad51582174b49d5d
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367695B2

Reaction notes

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