2-Methoxyethanol → HCID 58266777, compound

HRID 1505980Notes

Reaction equation

HRID 1505980 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:20]#[N:21])=[C:18]([OH:19])[C:13]=3[C:12]3[CH:22]=[C:23]([Br:26])[CH:24]=[N:25][C:11]2=3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:27][O:28][CH2:29][CH2:30]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>CN(C=O)C.C(OCC)(=O)C>[C:1]1([S:7]([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:20]#[N:21])=[C:18]([O:19][CH2:30][CH2:29][O:28][CH3:27])[C:13]=3[C:12]3[CH:22]=[C:23]([Br:26])[CH:24]=[N:25][C:11]2=3)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 80192-MethoxyethanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 582664728-(Benzenesulfonyl)-12-bromo-3-hydroxy-5,8,10-triazatricyclo[7.4.0.02,7]trideca-1(9),2,4,6,10,12-hexaene-4-carbonitrile

Product 1

HCID 58266777HCID 58266777, compoundYield 23.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 9-benzenesulfonyl-3-bromo-5-hydroxy-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (145 mg, 0.3 mmol), 2-methoxyethanol (158 μL, 2.0 mmol) and triphenylphosphine (525 mg, 2.0 mmol) in anhydrous DMF (1.25 mL) was treated with diethyl azodicarboxylate (0.315 mL, 2.0 mmol) and the mixture stirred at ambient temperature for 30 min then left to stand for 4 days. The mixture was diluted with ethyl acetate (20 mL) and washed with brine (3×10 mL) then the aqueous phase was extracted with ethyl acetate (10 mL). The combined organic phase was dried over magnesium sulfate and concentrated in vacuo. The resultant residue was purified by flash chromatography (silica, 5 g column, Si-SPE, 0-100% ethyl acetate in DCM) to afford the title compound (35 mg, 23%). 1H NMR (CDCl3, 300 MHz): 9.58 (s, 1H), 8.97 (d, J=2.3 Hz, 1H), 8.76 (d, J=2.3 Hz, 1H), 8.26-8.18 (m, 2H), 7.68-7.60 (m, 1H), 7.57-7.47 (m, 2H), 4.74-4.69 (m, 2H), 3.89-3.80 (m, 2H), 3.49 (s, 3H).

Workup

  1. waitthen left
  2. waitto stand for 4 days
  3. washwashed with brine (3×10 mL)
  4. extractionthe aqueous phase was extracted with ethyl acetate (10 mL)
  5. dry with materialThe combined organic phase was dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue was purified by flash chromatography (silica, 5 g column, Si-SPE, 0-100% ethyl acetate in DCM)

Sources & evidence

ORD record
ord-1733f769b77a4398aa80388234bdba10
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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