Ethanol → HCID 46205562, compound

HRID 1499019Notes

Reaction equation

HRID 1499019 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[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[O: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 87207622Pyrido[3′,2′:4,5]furo[3,2-d]pyrimidine, 2-chloro-4-(4-morpholinyl)-

Product 1

HCID 46205562HCID 46205562, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Under Ar(g), to a mixture of compound 5 (25 mg, 0.086 mmol), indole-4-boronic acid (15.2 mg, 0.095 mmol), dichloro-bis(triphenylphosphine)palladium (II) (3 mg, 0.004 mmol) and sodium hydrogen carbonate (22 mg, 0.26 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 45 min, 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 30-60% EtOAc/Hex) furnished B (24.5 mg, 0.067 mol, 77%) 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 30-60% EtOAc/Hex)
  7. customfurnished B (24.5 mg, 0.067 mol, 77%) as an off-white solid

Sources & evidence

ORD record
ord-b4c0ffc44cf940dbab89bd52451aa993
Source dataset
uspto-grants-2015_12
Patent number
US09200007B2

Reaction notes

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