Ethanol → HCID 50992289, compound

HRID 1499023Notes

Reaction equation

HRID 1499023 reaction equation
Br[C:2]1[CH:21]=[N:20][C:5]2[O:6][C:7]3[C:12]([N:13]4[CH2:18][CH2:17][O:16][CH2:15][CH2:14]4)=[N:11][C:10](Cl)=[N:9][C:8]=3[C:4]=2[CH:3]=1.[NH:22]1[C:30]2[CH:29]=[CH:28][CH:27]=[C:26](B(O)O)[C:25]=2[CH:24]=[CH:23]1.C(=O)([O-])O.[Na+].[CH2:39](O)[CH3:40]>O.C1(C)C=CC=CC=1>[NH:22]1[C:30]2[C:25](=[C:26]([C:10]3[N:11]=[C:12]([N:13]4[CH2:18][CH2:17][O:16][CH2:15][CH2:14]4)[C:7]4[O:6][C:5]5[N:20]=[CH:21][C:2]([C:40]6[CH:39]=[CH:28][CH:29]=[C:30]7[C:25]=6[CH:24]=[CH:23][NH:22]7)=[CH:3][C:4]=5[C:8]=4[N:9]=3)[CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23]1

Participants

7

Reactant 4

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 27631731H-Indole-4-boronic acidHCID 87207582HCID 87207582, compound

Product 1

HCID 50992289HCID 50992289, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Under Ar(g) to a mixture of compound 5 (8 mg, 0.022 mnnol), indole-4-boronic acid (10.5 mg, 0.065 mmol), dichloro-bis(triphenylphosphine)palladium (11) (1.5 mg, 0.002 mmol) and sodium hydrogen carbonate (8 mg, 0.097 mmol) was added ethanol (1 mL) followed by toluene (1.6 mL) and then water (0.5 mL). The reaction mixture was then heated in a microwave at 120° C. (300 W) for 1 h, and was subsequently cooled to rt; the mixture was then partitioned between CH2Cl2 and water, and the organic layer was separated, dried (MgSO4) and concentrated in vacuo. Purification by flash column chromatography on silica (eluant 20-40% EtOAc/Hex) furnished E (2.7 mg, 0.005 mol, 25%) as a yellow solid.

Workup

  1. temperaturewas subsequently cooled to rt
  2. customthe mixture was then partitioned between CH2Cl2 and water
  3. customthe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification by flash column chromatography on silica (eluant 20-40% EtOAc/Hex)
  7. customfurnished E (2.7 mg, 0.005 mol, 25%) as a yellow solid

Sources & evidence

ORD record
ord-5326faf561a44e3e905426f52e95d0a7
Source dataset
uspto-grants-2015_12
Patent number
US09200007B2

Reaction notes

Loading…