Trifluoroborane-methyl sulfide → HCID 45483052, compound

HRID 2390788Notes

Reaction equation

HRID 2390788 reaction equation
B(F)(F)F.CSC.[C:8]([C:11]1[CH:12]=[C:13]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[C:24]([C:31]4[CH:36]=[C:35]([CH3:37])[CH:34]=[C:33]([O:38]C)[CH:32]=4)=[N:25][N:26]([CH2:28][C:29]#[N:30])[CH:27]=3)=[CH:19][N:18]=2)[CH:14]=[CH:15][CH:16]=1)(=[O:10])[CH3:9]>ClCCl>[C:8]([C:11]1[CH:12]=[C:13]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[C:24]([C:31]4[CH:36]=[C:35]([CH3:37])[CH:34]=[C:33]([OH:38])[CH:32]=4)=[N:25][N:26]([CH2:28][C:29]#[N:30])[CH:27]=3)=[CH:19][N:18]=2)[CH:14]=[CH:15][CH:16]=1)(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 11137191Trifluoroborane-methyl sulfideHCID 45483024HCID 45483024, compound

Product 1

HCID 45483052HCID 45483052, 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 68 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 (39 mg, 69%).

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 (39 mg, 69%)

Sources & evidence

ORD record
ord-09009fc03e094444ac1aef483b2414d9
Source dataset
uspto-grants-2012_09
Patent number
US08273880B2

Reaction notes

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