Triethylamine → HCID 21186579, compound

HRID 1003612Notes

Reaction equation

HRID 1003612 reaction equation
BrC1(Br)C(=O)C2C(=CC(O[Si](C(C)C)(C(C)C)C(C)C)=C(C)C=2)OC1.[CH3:26][C:27]1[C:28]([Br:51])=[C:29]2[C:34](=[CH:35][C:36]=1[O:37][Si:38]([CH:45]([CH3:47])[CH3:46])([CH:42]([CH3:44])[CH3:43])[CH:39]([CH3:41])[CH3:40])[O:33][CH2:32][C:31](Br)(Br)[C:30]2=[O:50].[F:52][C:53]1[CH:58]=[CH:57][C:56]([C:59]2([OH:65])[CH2:64][CH2:63][NH:62][CH2:61][CH2:60]2)=[CH:55][CH:54]=1.C(N(CC)CC)C>C(#N)C>[Br:51][C:28]1[C:27]([CH3:26])=[C:36]([O:37][Si:38]([CH:39]([CH3:41])[CH3:40])([CH:42]([CH3:43])[CH3:44])[CH:45]([CH3:47])[CH3:46])[CH:35]=[C:34]2[C:29]=1[C:30](=[O:50])[C:31]([N:62]1[CH2:61][CH2:60][C:59]([C:56]3[CH:57]=[CH:58][C:53]([F:52])=[CH:54][CH:55]=3)([OH:65])[CH2:64][CH2:63]1)=[CH:32][O:33]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 774974-(4-Fluorophenyl)piperidin-4-olHCID 21186588HCID 21186588, compoundHCID 21186638HCID 21186638, compound

Product 1

HCID 21186579HCID 21186579, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3,3-dibromo-6-methyl-7-triisopropylsilyloxychroman-4-one and 6-methyl-3,3,5-tribromo-7-triisopropylsilyloxychroman-4-one (the compounds of Preparation 34, 1.0 g), 4-(4-fluorophenyl)-4-hydroxypiperidine (0.79 g, 4.05 mmol) and triethylamine (0.60 mL, 4.30 mmol) in acetonitrile (30 mL) was stirred 30 min at ambient temperature. The precipitate which formed was collected by filtration to afford 0.188 g of 5-bromo-6-methyl-7-triisopropylsilyloxy-3-(4-(4-fluorophenyl)-4-hydroxypiperidin-1-yl)-chromen-4-one. The filtrate was flash chromatographed on silica gel (1×4 inches packed in hexane) with elution proceeding as follows: 20% ethyl acetate/hexane (100 mL), 0.115 g of 6-methyl -7-triisopropylsilyloxy-3-(4-(4-fluorophenyl)-4-hydroxypiperidin-1-yl)-chromen-4-one as a light yellow solid which had mp 193-195° C.; 20% ethyl acetate/hexane (100 mL) and 40% ethyl acetate/hexane (100 mL), 0.07 g of a mixture; 40% ethyl acetate/hexane (100 mL) and 60% ethyl acetate/hexane (400 mL), 0.30 g of 6-methyl-7-hydroxy-3-(4-(4-fluorophenyl)-4-hydroxypiperidin-1-yl)-chromen-4-one.

Workup

  1. customThe precipitate which formed
  2. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-e8d388ba44b84355980e51a770b5f8a5
Source dataset
uspto-grants-2000_04
Patent number
US06046213

Reaction notes

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