Potassium Fluoride → HCID 58909417, compound

HRID 1296145Notes

Reaction equation

HRID 1296145 reaction equation
C1(C2C=CC=CC=2)C=CC=CC=1P(C(C)(C)C)C(C)(C)C.Br[C:23]1[CH:24]=[C:25]([C:29]2([NH:35][CH2:36][C@@H:37]([OH:52])[C@@H:38]([NH:48][C:49](=[O:51])[CH3:50])[CH2:39][C:40]3[CH:45]=[C:44]([F:46])[CH:43]=[C:42]([F:47])[CH:41]=3)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[CH:26]=[CH:27][CH:28]=1.[CH3:53][C:54]1[CH:55]=[C:56](B(O)O)[S:57][CH:58]=1.[F-].[K+]>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:47][C:42]1[CH:41]=[C:40]([CH:45]=[C:44]([F:46])[CH:43]=1)[CH2:39][C@H:38]([NH:48][C:49](=[O:51])[CH3:50])[C@H:37]([OH:52])[CH2:36][NH:35][C:29]1([C:25]2[CH:26]=[CH:27][CH:28]=[C:23]([C:56]3[S:57][CH:58]=[C:54]([CH3:53])[CH:55]=3)[CH:24]=2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

7

Reactant 4

HCID 522689Potassium FluorideHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 27343734-Methylthiophene-2-boronic acidHCID 58909340HCID 58909340, compound

Product 1

HCID 58909417HCID 58909417, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Palladium acetate (Pd(OAc)2) (0.82 mgs, 10 mol. Wt. %) and Biphenyl-2-yl-di-tert-butyl-phosphane (2.16 mgs, 20 mol. Wt. %) was added to the reaction vessel (Vessel 1). N-(1S,2R)-[3-[1-(3-Bromo-phenyl)-cyclohexylamino]-1-(3,5-difluoro-benzyl)-2-hydroxy-propyl]-acetamide (0.09075 mM) was placed in a separate reaction vessel (Vessel 2) and dissolved in 200 mL DME. 4-Methylthiophene-2-boronic acid and Potassium Fluoride (KF) (3 eq., 6.33 mgs) were added to a separate reaction vessel and dissolved in 200 μL DME (Vessel 3). Solvents in Vessels 2 and 3 were added to Vessel 1 under nitrogen. Vessel 1 was stirred over night at room temperature. Reaction was then concentrated down by vacuum. Crude material purified by Prep-HPLC. Product fractions collected and concentrated down by vacuum. MS (ESI+) for C29H34F2N2O2S m/z 513.0 (M+H)+

Workup

  1. additionSolvents in Vessels 2 and 3 were added to Vessel 1 under nitrogen
  2. customReaction
  3. concentrationwas then concentrated down by vacuum
  4. customCrude material purified by Prep-HPLC
  5. customProduct fractions collected
  6. concentrationconcentrated down by vacuum

Sources & evidence

ORD record
ord-36845fdb85cb4f3c8466404305184b8e
Source dataset
uspto-grants-2007_07
Patent number
US07244725B2

Reaction notes

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