Tetrabutylammonium Fluoride → HCID 68549849, compound

HRID 1446092Notes

Reaction equation

C([SiH2][O:6][C:7](C)(C)[CH:8]1[O:12][C:11](=[O:13])[N:10]([C:14]2[CH:19]=[CH:18][C:17](B3OC(C)(C)C(C)(C)O3)=[C:16]([F:29])[CH:15]=2)[CH2:9]1)(C)(C)C.Br[C:33]1[CH:34]=[CH:35][C:36]([C:39]2([CH3:50])[O:43][C:42]3=[N:44][C:45]([N+:47]([O-:49])=[O:48])=[CH:46][N:41]3[CH2:40]2)=[N:37][CH:38]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[F:29][C:16]1[CH:15]=[C:14]([N:10]2[CH2:9][CH:8]([CH2:7][OH:6])[O:12][C:11]2=[O:13])[CH:19]=[CH:18][C:17]=1[C:33]1[CH:38]=[N:37][C:36]([C:39]2([CH3:50])[O:43][C:42]3=[N:44][C:45]([N+:47]([O-:49])=[O:48])=[CH:46][N:41]3[CH2:40]2)=[CH:35][CH:34]=1

Participants

Reactant 3

HCID 2724141Tetrabutylammonium Fluoride

HCID 68546001HCID 68546001, compound

HCID 131727902HCID 131727902, compound

Product 1

HCID 68549849HCID 68549849, compound

Procedure

The titled compound was prepared using the same procedure as described previously (see Example 2-1, Step 3), except that 5-(tert-Butyl-dimethyl-silanyloxymethyl)-3-[3-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-oxazolidin-2-one, and 2-(5-Bromo-pyridin-2-yl)-2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazole were used as the starting materials, and TBAF deprotection required. The titled compound was obtained as slightly yellow solid (60 mg). ESI MS m/z 456 (M+H). 1H NMR (DMSO-d6) δ 8.79 (s, 1H), 8.14 (s, 1H), 8.05-8.12 (m, 1H), 7.75 (d, J=8.8 Hz, 1H), 7.63 (dd, J=5.2, 2.8 Hz, 1H), 7.48 (dd, J=8.8, 2.0 Hz, 1H), 5.24 (t, J=5.6 Hz, 1H), 4.85 (d, J=10.8 Hz, 1H), 4.69-4.77 (m, 1H), 4.49 (d, J=10.8 Hz, 1H), 4.12 (t, J=8.8 Hz, 1H), 3.86 (dd, J=8.8, 5.6 Hz, 1H), 3.64-3.72 (m, 1H), 3.50-3.59 (m, 1H), 1.97 (s, 3H).

Workup

customThe titled compound was prepared

Sources & evidence

ORD record: ord-5a6c616e056841049786e4206e6ac7ea
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666864B2

Reaction notes

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