Tetrahydrofuran → HCID 86643170, compound

HRID 2070046Notes

Reaction equation

HRID 2070046 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][C:9]([O:10][C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]4[CH:26]=[CH:25][C:24]([CH:27]=C)=[C:23]([C:29]([F:32])([F:31])[F:30])[CH:22]=4)=[O:19])=[CH:13][CH:12]=3)=[C:4]2[CH:3]=[CH:2]1.C1C[O:36]CC1>O.[Os](=O)(=O)(=O)=O>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][C:9]([O:10][C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]4[CH:26]=[CH:25][C:24]([CH:27]=[O:36])=[C:23]([C:29]([F:32])([F:30])[F:31])[CH:22]=4)=[O:19])=[CH:13][CH:12]=3)=[C:4]2[CH:3]=[CH:2]1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 16113023HCID 16113023, compound

Product 1

HCID 86643170HCID 86643170, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

1-[4-(1H-Pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]-3-(3-trifluoromethyl-4-vinylphenyl)urea (300 mg, 0.68 mmol) was dissolved in a solution mixture of THF (100 mL) and water (50 mL), and an osmium tetraoxide aqueous solution (0.1 M, 300 μL) and sodium periodide (590 mg, 2.76 mmol) were added thereto. The resulting mixture was stirred at room temperature for 17 hours. The reaction solution was partitioned between ethyl acetate and water. The organic layer was washed with saturated brine and concentrated under reduced pressure to give a crude product of 1-[4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]-3-(3-trifluoromethyl-4-formylphenyl)urea (229 mg, 76%). Then, this crude formyl compound (59.4 mg, 0.14 mmol) was dissolved in methanol (3 mL), and sodium borohydride (15.5 mg, 0.41 mmol) was added thereto. The resulting mixture was stirred at room temperature for 2 hours. The reaction solution was partitioned between ethyl acetate and water. The organic layer was washed with saturated brine and concentrated under reduced pressure to give a crude product of 1-[4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]-3-(3-trifluoromethyl-4-hydroxymethylphenyl)urea (50.9 mg, 85%).

Workup

  1. customThe reaction solution was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with saturated brine
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-914bb6cd66ad4c459df0118a0402ffb2
Source dataset
uspto-grants-2012_10
Patent number
US08299252B2

Reaction notes

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