Trifluoroborane-methyl sulfide → HCID 45483044, compound

HRID 2390781Notes

Reaction equation

HRID 2390781 reaction equation
B(F)(F)F.CSC.C[O:9][C:10]1[CH:11]=[C:12]([C:17]2[N:21]([CH2:22][C:23]#[N:24])[N:20]=[CH:19][C:18]=2[C:25]2[CH:30]=[CH:29][N:28]=[C:27]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([NH:37][C:38](=[O:40])[CH3:39])[CH:32]=3)[CH:26]=2)[CH:13]=[C:14]([CH3:16])[CH:15]=1>ClCCl>[OH:9][C:10]1[CH:11]=[C:12]([C:17]2[N:21]([CH2:22][C:23]#[N:24])[N:20]=[CH:19][C:18]=2[C:25]2[CH:30]=[CH:29][N:28]=[C:27]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([NH:37][C:38](=[O:40])[CH3:39])[CH:32]=3)[CH:26]=2)[CH:13]=[C:14]([CH3:16])[CH:15]=1

Participants

4

Reactant 2

HCID 11137191Trifluoroborane-methyl sulfideHCID 45482661HCID 45482661, compound

Product 1

HCID 45483044HCID 45483044, 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 (52.5 mg, 0.12 mmol) prepared in Example 39 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 (28 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 (28 mg, 55%)

Sources & evidence

ORD record
ord-0b8f3d380b0b4a9a8caef67e91d0cd30
Source dataset
uspto-grants-2012_09
Patent number
US08273880B2

Reaction notes

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