Methanol → HCID 57397896, compound

HRID 1177660Notes

Reaction equation

HRID 1177660 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]=[CH:9][N+:10]([O-])=O)[CH:5]=[CH:4][C:3]=1[C:13]1[S:14][C:15]2[C:20]([N:21]=1)=[CH:19][CH:18]=[C:17]([C:22]1([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:24][CH2:23]1)[N:16]=2.C1COCC1.CO.O>[Zn].C(O)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][NH2:10])[CH:5]=[CH:4][C:3]=1[C:13]1[S:14][C:15]2[C:20]([N:21]=1)=[CH:19][CH:18]=[C:17]([C:22]1([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:23][CH2:24]1)[N:16]=2

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 8028TetrahydrofuranHCID 67111881HCID 67111881, compound

Product 1

HCID 57397896HCID 57397896, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
65 °C

Procedure

To 2-(2-fluoro-4-(2-nitrovinyl)phenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine (0.788 g, 1.89 mmol) was added THF (9.44 mL), methanol (9.44 mL), water (9.44 mL), and acetic acid (9.44 mL) before zinc (0.987 g, 15.1 mmol) was added. The reaction mixture was heated to 65° C. for 18 h. The reaction mixture was concentrated, neutralized with aq NaHCO3, and extracted with DCM. The organic layer was concentrated, filtered, washed with water, and dried in a vacuum oven to give the title compound after purification via preparatory LC. MS (ESI) m/z: Calculated: 389.1; Observed: 380.1 (M++H).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with DCM
  4. concentrationThe organic layer was concentrated
  5. filtrationfiltered
  6. washwashed with water
  7. customdried in a vacuum oven

Sources & evidence

ORD record
ord-86ceca96553749e3985faa39b7097cba
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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