HCID 66578809, compound → HCID 66581100, compound

HRID 1521830Notes

Reaction equation

HRID 1521830 reaction equation
[C:1]1([N:7]2[C:11]3[C:12]4[C:17]([S:18](=[O:21])(=[O:20])[CH2:19][C:10]=3[C:9]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N:8]2)=[CH:16][CH:15]=[N+:14]([O-])[CH:13]=4)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(=O)C.[Fe]>[C:1]1([N:7]2[C:11]3[C:12]4[C:17]([S:18](=[O:20])(=[O:21])[CH2:19][C:10]=3[C:9]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N:8]2)=[CH:16][CH:15]=[N:14][CH:13]=4)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 66578809HCID 66578809, compound

Product 1

HCID 66581100HCID 66581100, compoundYield 83.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of ethyl 1-phenyl-1,4-dihydropyrazolo[3′,4′:4,5]thiopyrano[3,2-c]pyridine-3-carboxylate 5,5,8-trioxide (0.1 g, 0.259 mmol) in glacial acetic acid is added iron powder (58 mg, 1.038 mmol) under nitrogen and the reaction mass is heated to 85° C. for 1 h. The reaction mass is concentrated completely under reduced pressure and is partitioned between water and ethylacetate. The organic layer is separated, dried using sodium sulphate and is concentrated under reduced pressure to afford 80 mg, 83% yield of the title compound. 1H NMR (400 MHz, DMSO-d6) δ=8.85-8.84 (d, J=5.2 Hz, 1H), 8.00-7.98 (m, 2H), 7.68-7.66 (m, 3H), 7.61 (m,1H), 5.12 (s, 2H), 4.38-4.36 (q, 2H), 1.35-1.32 (t, J=7.12 Hz, 3H). MS (ESI+): 370.0.

Workup

  1. concentrationThe reaction mass is concentrated completely under reduced pressure
  2. customis partitioned between water and ethylacetate
  3. customThe organic layer is separated
  4. customdried
  5. concentrationis concentrated under reduced pressure

Sources & evidence

ORD record
ord-f05c79cf943b4cd98a94a59a482406ac
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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