Potassium Carbonate → Formate

HRID 1958828Notes

Reaction equation

Br[CH2:2][CH2:3][O:4][Si](C(C)(C)C)(C)C.C([C:14]1[CH:19]=[C:18]([C:20]2[N:24]=[C:23]([C:25]3[CH:30]=[C:29]([CH3:31])[CH:28]=[C:27]([CH2:32][N:33]([CH2:35][CH3:36])[CH3:34])[CH:26]=3)[O:22][N:21]=2)[CH:17]=[C:16]([CH3:37])[C:15]=1[OH:38])C.[C:39]([O-])([O-:41])=[O:40].[K+].[K+]>C(#N)C>[CH2:35]([N:33]([CH2:32][C:27]1[CH:26]=[C:25]([C:23]2[O:22][N:21]=[C:20]([C:18]3[CH:17]=[C:16]([CH3:37])[C:15]([O:38][CH2:2][CH2:3][OH:4])=[C:14]([CH3:39])[CH:19]=3)[N:24]=2)[CH:30]=[C:29]([CH3:31])[CH:28]=1)[CH3:34])[CH3:36].[CH:39]([O-:41])=[O:40]

Participants

Conditions

Temperature: 70 °C

Procedure

(2-bromoethoxy)-tert-butyl-dimethylsilane (104 mg, 435 μmol) was added to a suspension of 2-ethyl-4-(5-{3-[(ethyl-methyl-amino)-methyl]-5-methyl-phenyl}-[1,2,4]oxadiazol-3-yl)-6-methyl-phenol (53 mg, 145 μmol) and K2CO3 (60 mg, 435 μmol) in acetonitrile (2 mL). The mixture was stirred at 70° C. for 16 h before it was filtered. The filtrate was diluted with 1N aq. HCl (0.1 mL) and 2N aq. HCl (0.1 mL). The mixture was allowed to stand at rt for 10 min before the solvent was removed in vacuo. The crude product was purified by prep. HPLC to give the title compound as a formate salt in the form of a white lyphilisate (29 mg). LC-MS: tR=0.59 min; [M+1]+=410.26; 1H NMR (D6-DMOS): δ 1.06 (t, J=7.3 Hz, 3H), 1.23 (t, J=7.3 Hz, 3H), 2.15 (s, 3H), 2.36 (s, 3H), 2.42-2.48 (m, 5H), 2.75 (q, J=7.5 Hz, 2H), 3.56 (s, 2H), 3.73-3.77 (m, 2H), 3.84-3.89 (m, 2H), 7.47 (s, 1H), 7.80 (s, 2H), 7.90 (s, 1H), 7.92 (s, 1H), 8.17 (s, 1H, formate).

Workup

filtrationwas filtered
additionThe filtrate was diluted with 1N aq. HCl (0.1 mL) and 2N aq. HCl (0.1 mL)
waitto stand at rt for 10 min before the solvent
customwas removed in vacuo
customThe crude product was purified by prep

Sources & evidence

ORD record: ord-52f785f76a7e40f8af51c13d2a70045f
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410151B2

Reaction notes

Loading…