Sodium Chloride → HCID 67960063, compound

HRID 1529383Notes

Reaction equation

HRID 1529383 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([C:19]5[CH:24]=[N:23][CH:22]=[C:21]([CH:25]6[CH2:27][CH2:26]6)[N:20]=5)[CH:17]=4)[N:12](S(C4C=CC(C)=CC=4)(=O)=O)[CH:11]=3)[CH:7]=[N:6][CH:5]=2)[CH2:3][CH2:2]1.[OH-].[Na+].[Na+].[Cl-]>O1CCOCC1.CCOC(C)=O>[CH:1]1([C:4]2[N:9]=[C:8]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([C:19]5[CH:24]=[N:23][CH:22]=[C:21]([CH:25]6[CH2:27][CH2:26]6)[N:20]=5)[CH:17]=4)[NH:12][CH:11]=3)[CH:7]=[N:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 67959693HCID 67959693, compound

Product 1

HCID 67960063HCID 67960063, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A glass microwave reaction vessel was charged with 3,5-bis(6-cyclopropylpyrazin-2-yl)-1-tosyl-1H-indole (72 mg, 0.14 mmol) and 1 M NaOH (aq., 0.71 mL, 0.71 mmol) in dioxane (1.5 mL). The reaction was stirred and heated in a Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 120° C. for 20 min. Saturated NaCl (aq.) was added and the mixture was extracted with EtOAc (3×). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated. The crude product was purified by silica gel chromatography, eluting with a gradient of 0-70% EtOAc in hexanes, to the title compound (25 mg, 0.07 mmol, 50% yield) as a light-yellow solid. MS (ESI, pos. ion) m/z: 354.1 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.90 (s, 1H), 9.07-9.14 (m, 1H), 8.95 (d, J=6.46 Hz, 2H), 8.53 (s, 1H), 8.37 (d, J=3.91 Hz, 2H), 7.89-7.97 (m, 1H), 7.60 (s, 1H), 2.22-2.33 (m, 2H), 1.06-1.26 (m, 8H).

Workup

  1. customA glass microwave reaction vessel
  2. extractionthe mixture was extracted with EtOAc (3×)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1f6934f301264a9283ed757a8a4f6804
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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