Ethanol → HCID 50992288, compound

HRID 1499022Notes

Reaction equation

HRID 1499022 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[O: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[N:28]=[CH:27][CH:26]=[C:25](B3OC(C)(C)C(C)(C)O3)[C:24]=2[CH:23]=[CH:22]1.C(=O)([O-])O.[Na+].C(O)C>O.C1(C)C=CC=CC=1>[N:15]1([C:4]2[C:5]3[O:10][C:9]4[N:11]=[CH:12][CH:13]=[CH:14][C:8]=4[C:6]=3[N:7]=[C:2]([C:25]3[CH:26]=[CH:27][N:28]=[C:29]4[NH:21][CH:22]=[CH:23][C:24]=34)[N:3]=2)[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 497588714-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridineHCID 87207622Pyrido[3′,2′:4,5]furo[3,2-d]pyrimidine, 2-chloro-4-(4-morpholinyl)-

Product 1

HCID 50992288HCID 50992288, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Under Ar(g) to a mixture of compound 5 (20 mg, 0.069 mmol), 7-azaindole-4-boronic acid pinacol ester (18.5 mg, 0.076 mmol), dichloro-bis(triphenylphosphine)palladium (II) (2.4 mg, 0.003 mmol) and sodium hydrogen carbonate (17.4 mg, 0.21 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 30-90% EtOAc/Hex) furnished D (20 mg, 0.054 mol, 78%) as an off-white 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 30-90% EtOAc/Hex)
  7. customfurnished D (20 mg, 0.054 mol, 78%) as an off-white solid

Sources & evidence

ORD record
ord-1ead4573c046434e9ccda8be75443554
Source dataset
uspto-grants-2015_12
Patent number
US09200007B2

Reaction notes

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