Ethanol → HCID 136360287, compound

HRID 1262383Notes

Reaction equation

HRID 1262383 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1.Br[C:26]1[N:34]2[C:29]([CH:30]=[N:31][C:32]([S:35][CH3:36])=[N:33]2)=[CH:28][CH:27]=1.[OH:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>[Cl-].[Na+].O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:36][S:35][C:32]1[N:31]=[CH:30][C:29]2=[CH:28][CH:27]=[C:26]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=3[OH:37])[N:34]2[N:33]=1

Participants

9

Reactant 6

HCID 702EthanolHCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 2773454(2-Hydroxyphenyl)boronic acidHCID 574161287-Bromo-2-(methylsulfanyl)pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 136360287HCID 136360287, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 57417360Sodium chloride; waterSolvent

Procedure

Palladium Acetate (0.365 g, 0.00162 mol) and Triphenylphosphine (0.442 g, 0.00168 mol) were dissolved in Tetrahydrofuran (20 mL, 0.3 mol) and the mixture was stirred at room temperature for 10 minutes. 7-Bromo-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (1.943 g, 0.007959 mol) was added and the reaction was stirred for another 10 minutes. 2-hydroxyphenyl boronic acid (3.09 g, 0.022 mol) was added followed by saturated sodium carbonate solution (7.6 mL) and Ethanol (20 mL, 0.4 mol;). The reaction mixture was heated at 80° C. for 2 days. Brine was poured into the reaction mixture and organics were extracted three times into ethyl acetate. Combined organic layers were dried over sodium sulfate, filtered, concentrated and purified by normal phase silica gel chromatography eluting with ethyl acetate/heptane to yield a yellow solid, 2-(2-Methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenol (1.92 g, 94%). LCMS: m/z=258.02 (M+H+); 1H NMR (400 MHz, DMSO-d6) δ 9.84 (s, 1H), 8.97 (s, 1H), 7.87 (m, 1H), 7.22 (d, 1H, J=4.7 Hz), 7.12 (m, 1H), 7.05 (d, 1H, J=4.7 Hz), 7.01 (d, 1H, J=7.8 Hz), 6.93 (m, 1H), 2.47 (s, 3H).

Workup

  1. stirringthe reaction was stirred for another 10 minutes
  2. temperatureThe reaction mixture was heated at 80° C. for 2 days
  3. extractionorganics were extracted three times into ethyl acetate
  4. dry with materialCombined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by normal phase silica gel chromatography
  8. washeluting with ethyl acetate/heptane

Sources & evidence

ORD record
ord-ac93d9c172e84a5daae7cdd26c220e20
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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