Acetic Acid → HCID 67111881, compound

HRID 1177659Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][CH:15]=[C:14]([C:19]1([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:21][CH2:20]1)[N:13]=2)[CH:5]=O.C(O)(=O)C.[N+:32]([CH3:35])([O-:34])=[O:33].C([O-])(=O)C.[NH4+]>O>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:35][N+:32]([O-:34])=[O:33])[CH:7]=[CH:8][C:9]=1[C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][CH:15]=[C:14]([C:19]1([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:20][CH2:21]1)[N:13]=2

Participants

Conditions

Temperature: 100 °C

Procedure

To 3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde (1.42 g, 3.79 mmol) was added acetic acid (12.6 mL), nitromethane (1.44 mL, 26.5 mmol), and ammonium acetate (0.731 g, 9.48 mmol) before it was stirred at 100° C. for 4 h. The reaction mixture was cooled to ambient temperature. The product crashed out with water, and was filtered, washed with water, and dried in a vacuum oven to give 2-(2-fluoro-4-(2-nitrovinyl)phenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine. MS (ESI) m/z: Calculated: 417.1; Observed: 418.4 (M++H).

Workup

temperatureThe reaction mixture was cooled to ambient temperature
filtrationwas filtered
washwashed with water
customdried in a vacuum oven

Sources & evidence

ORD record: ord-2a77d2a904f545cabd41d20a718eb071
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842685B2

Reaction notes

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