1-Butanaminium, N,N,N-tributyl-, fluoride, hydrate → N,N-di(1,1-dimethylethoxycarbonyl)-3-(1-(2,3-difluorophenyl)-1H-tetrazol-5-yl)-5-ethynylpyridin-2-amine

HRID 254014Notes

Reaction equation

[CH3:1][C:2]([CH3:40])([O:4][C:5]([N:7]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:8]1[C:13]([C:14]2[N:18]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=3[F:26])[N:17]=[N:16][N:15]=2)=[CH:12][C:11]([C:27]#[C:28][Si](C)(C)C)=[CH:10][N:9]=1)=[O:6])[CH3:3].O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl>[CH3:38][C:36]([CH3:39])([O:35][C:33]([N:7]([C:5]([O:4][C:2]([CH3:40])([CH3:3])[CH3:1])=[O:6])[C:8]1[C:13]([C:14]2[N:18]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=3[F:26])[N:17]=[N:16][N:15]=2)=[CH:12][C:11]([C:27]#[CH:28])=[CH:10][N:9]=1)=[O:34])[CH3:37]

Participants

Conditions

Temperature: 0 °C

Procedure

N,N-Di(1,1-dimethylethoxycarbonyl)-3-(1-(2,3-difluorophenyl)-1H-tetrazol-5-yl)-5-(2-(trimethylsilyl)ethynyl)pyridin-2-amine (713 mg, 1.2 mmol) was dissolved in methylene chloride (10 mL) and cooled to 0° C. To this was added tetrabutylammonium fluoride hydrate (163 mg, 625 μmol) in methylene chloride (1 mL). The reaction was loaded directly onto silica and chromatographed (10% ethyl acetate/hexane to 50% ethyl acetate/hexane) to give N,N-di(1,1-dimethylethoxycarbonyl)-3-(1-(2,3-difluorophenyl)-1H-tetrazol-5-yl)-5-ethynylpyridin-2-amine (496 mg, 1.0 mmol, 83%) as a yellow solid; 1H NMR (CDCl3): 1.37 (s, 18H), 3.35 (s, 1H), 7.30 (m, 1H), 7.40 (m, 2H), 7.89 (s, 1H), 8.75 (s, 1H).

Workup

customchromatographed (10% ethyl acetate/hexane to 50% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-7b3de68b84d94b51b0d667bcb3a66dde
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07872031B2

Reaction notes

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