Water → HCID 43518238, compound

HRID 1946844Notes

Reaction equation

HRID 1946844 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[N+:13]([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+].O.O1CCOCC1>C1COCC1>[NH2:13][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:5]=1[O:4][C:3]1[CH:16]=[C:17]([CH3:20])[CH:18]=[CH:19][C:2]=1[CH3:1])[C:9]#[N:10]

Participants

6

Reactant 4

HCID 962WaterHCID 24489Sodium DithioniteHCID 312751,4-DioxaneHCID 27815831HCID 27815831, compound

Product 1

HCID 43518238HCID 43518238, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The coupled product 30 (12.00 g, 44.73 mmol) was reduced with sodium hydrosulfite (30.47 g, 175.00 mmol) in a mixture of THF (75 mL), water (100 mL), and dioxane (45 mL). After the reaction is complete, volatile organic solvents were removed in vacuo and the precipitate in the remaining water was collected via vacuum filtration to afford compound 31 as a white solid (9.50 g, 89.0% yield, 99.5% pure). 1H NMR (500 MHz, DMSO-d6): δ 7.19 (d, J=8 Hz, 1H), 7.07 (d, J=2 Hz, 1H), 6.94 (d, J=8 Hz, 1H), 6.86 (dd, J1=8 Hz, J2=2 Hz, 1H), 6.74 (s, 1H), 6.45 (d, J=8 Hz, 1H), 5.52 (s, 2H), 2.23 (s, 3H), 2.08 (s, 3H).

Workup

  1. customvolatile organic solvents were removed in vacuo
  2. filtrationthe precipitate in the remaining water was collected via vacuum filtration

Sources & evidence

ORD record
ord-56131b32b60b454db1a261b19c0c7786
Source dataset
uspto-grants-2013_03
Patent number
US08399456B2

Reaction notes

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