Trifluoroborane-methyl sulfide → HCID 45483051, compound

HRID 2390786Notes

Reaction equation

HRID 2390786 reaction equation
B(F)(F)F.CSC.[C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24]([C:31]3[CH:36]=[C:35]([CH3:37])[CH:34]=[C:33]([O:38]C)[CH:32]=3)=[N:25][N:26]([CH2:28][C:29]#[N:30])[CH:27]=2)=[CH:19][N:18]=1)(=[O:10])[CH3:9]>ClCCl>[C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24]([C:31]3[CH:36]=[C:35]([CH3:37])[CH:34]=[C:33]([OH:38])[CH:32]=3)=[N:25][N:26]([CH2:28][C:29]#[N:30])[CH:27]=2)=[CH:19][N:18]=1)(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 11137191Trifluoroborane-methyl sulfideHCID 45483017HCID 45483017, compound

Product 1

HCID 45483051HCID 45483051, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Borontrifluoride-dimethylsulfide (0.13 mL, 1.2 mmol) was dropwise added to a solution of the methoxy compound (50.7 mg, 0.12 mmol) prepared in Example 67 in dichloromethane (4 mL) at room temperature under nitrogen atmosphere, and stirred for 24 hours. The reaction mixture was concentrated by vacuum distillation. The residue was treated in ethyl acetate (100 mL) and brine (50 mL), and the organic layer was dried over anhydrous magnesium sulfate and distilled under vacuum. Purification through column chromatography (silica gel, ethyl acetate) afforded pure hydroxy products (27 mg, 55%).

Workup

  1. concentrationThe reaction mixture was concentrated by vacuum distillation
  2. additionThe residue was treated in ethyl acetate (100 mL)
  3. dry with materialbrine (50 mL), and the organic layer was dried over anhydrous magnesium sulfate
  4. distillationdistilled under vacuum
  5. customPurification through column chromatography (silica gel, ethyl acetate)
  6. customafforded pure hydroxy products (27 mg, 55%)

Sources & evidence

ORD record
ord-cb489d01688c4816835b7c4fc913bd88
Source dataset
uspto-grants-2012_09
Patent number
US08273880B2

Reaction notes

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