Sodium t-butoxide → HCID 67111934, compound

HRID 1177611Notes

Reaction equation

[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH3:9])=[O:7])[N:3]=[CH:2]1.[CH3:10][C:11]([CH3:14])([O-:13])C.[Na+].Br[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[S:25][C:26]3[C:31]([N:32]=2)=[CH:30][CH:29]=[C:28]([C:33]2([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH2:35][CH2:34]2)[N:27]=3)=[C:20]([F:42])[CH:19]=1>C(O)C>[F:42][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][C:21]=1[C:24]1[S:25][C:26]2[C:31]([N:32]=1)=[CH:30][CH:29]=[C:28]([C:33]1([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:35][CH2:34]1)[N:27]=2)[CH2:17][N:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[N:3]=[CH:2]1.[F:42][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][C:21]=1[C:24]1[S:25][C:26]2[C:31]([N:32]=1)=[CH:30][CH:29]=[C:28]([C:33]1([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH2:35][CH2:34]1)[N:27]=2)[CH2:17][N:3]1[C:4]([C:6]([O:13][CH2:11][CH3:14])=[O:7])=[CH:5][N:1]=[CH:2]1

Participants

Conditions

Temperature: 70 °C

Procedure

In a reactor tube was dissolved methyl 4-imidazolecarboxylate (0.047 g, 0.37 mmol) in ethyl alcohol (2 mL). To the solution was added sodium tert-butoxide (0.035 g, 0.37 mmol) followed by 2-(4-(bromomethyl)-2-fluorophenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine (0.081 g, 0.18 mmol) and the reaction mixture was heated to 70° C. for 1 h. The crude reaction mixture was concentrated in vacuo and purified by silica gel chromatography to afford pure ethyl 1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzyl)-1H-imidazole-4-carboxylate and ethyl 1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzyl)-1H-imidazole-5-carboxylate. MS (ESI) m/z: calculated: 498.2; Observed: 499.0.

Workup

customThe crude reaction mixture
concentrationwas concentrated in vacuo
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-4caee61454fd4289b528a04b64825575
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842685B2

Reaction notes

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