Ethanol → HCID 50992286, compound

HRID 1499017Notes

Reaction equation

HRID 1499017 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]2[S:10][C:9]3[N:11]=[CH:12][CH:13]=[CH:14][C:8]=3[C:6]=2[N:7]=1.[NH:21]1[C:29]2[CH:28]=[CH:27][CH:26]=[C:25](B(O)O)[C:24]=2[CH:23]=[CH:22]1.C(=O)([O-])O.[Na+].C(O)C>O.C1(C)C=CC=CC=1>[NH:21]1[C:29]2[C:24](=[C:25]([C:2]3[N:3]=[C:4]([N:15]4[CH2:20][CH2:19][O:18][CH2:17][CH2:16]4)[C:5]4[S:10][C:9]5[N:11]=[CH:12][CH:13]=[CH:14][C:8]=5[C:6]=4[N:7]=3)[CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22]1

Participants

7

Reactant 4

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 27631731H-Indole-4-boronic acidHCID 87207693HCID 87207693, compound

Product 1

HCID 50992286HCID 50992286, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Under Ar(g), to a mixture of compound 5 (14.97 mg, 0.049 mmol), indole-4-boronic acid (8.70 mg, 0.054 mmol), dichloro-bis(triphenylphosphine)palladium (II) (1.81 mg, 0.0026 mmol) and sodium hydrogen carbonate (12.50 mg, 0.15 mmol) was added ethanol (0.75 mL) followed by toluene (1.25 mL) and then water (0.35 mL). The reaction was then heated in a microwave at 120° C. (300 W) for 1 h. The reaction nl/xtuvevvas then cooled to rt, and was partitioned between CH2Cl2 and water, and the organic layer was then separated, dried (MgSO4) and concentrated in vacuo. Purification by flash column chromatography on silica (eluant 0:1-1:99) MeOH/CH2Cl2) furnished A (1 mg, 0.0026 mol, 5%) as a white solid.

Workup

  1. customThe reaction nl/xtuvevvas
  2. temperaturecooled to rt
  3. customwas partitioned between CH2Cl2 and water
  4. customthe organic layer was then separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customPurification by flash column chromatography on silica (eluant 0:1-1:99) MeOH/CH2Cl2)
  8. customfurnished A (1 mg, 0.0026 mol, 5%) as a white solid

Sources & evidence

ORD record
ord-d9b2be0dda394cbbac5e0eedca680e05
Source dataset
uspto-grants-2015_12
Patent number
US09200007B2

Reaction notes

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