Triethylamine → HCID 10168896, compound

HRID 352990Notes

Reaction equation

HRID 352990 reaction equation
[OH:1][CH:2]([C:5]1[CH:10]=[C:9]([I:11])[N:8]([CH2:12][C:13]#[CH:14])[C:7](=[O:15])[C:6]=1[CH3:16])[CH2:3][CH3:4].CCN(CC)CC.Br[Si:25]([CH:44]([CH3:46])[CH3:45])([CH:41]([CH3:43])[CH3:42])[CH2:26][CH2:27][C:28]([F:40])([F:39])[C:29]([F:38])([F:37])[C:30]([F:36])([F:35])[C:31]([F:34])([F:33])[F:32]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH:44]([Si:25]([CH:41]([CH3:43])[CH3:42])([CH2:26][CH2:27][C:28]([F:40])([F:39])[C:29]([F:37])([F:38])[C:30]([F:35])([F:36])[C:31]([F:32])([F:33])[F:34])[O:1][CH:2]([C:5]1[CH:10]=[C:9]([I:11])[N:8]([CH2:12][C:13]#[CH:14])[C:7](=[O:15])[C:6]=1[CH3:16])[CH2:3][CH3:4])([CH3:45])[CH3:46]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 22706711HCID 22706711, compoundHCID 86594466HCID 86594466, compound

Product 1

HCID 10168896HCID 10168896, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(1-hydroxypropyl)-6-iodo-3-methyl-1-prop-2-ynyl-1H-pyridin-2-one 4b (44 mg, 0.13 mmol) and 4-dimethylaminopyridine (2 mg, 1.2 μmol) in CH2Cl2 (2 mL) was added NEt3 (53 mg, 74 μL, 0.52 mmol) and bromodiisopropyl(3, 3, 4, 4, 5, 5, 6, 6, 6-nonafluorohexyl)silane (147 mg, 0.33 mmol, prepared by mixing diisopropyl-(3, 3, 4, 4, 5, 5, 6, 6, 6-nonafluorohexyl)silane and Br2) and the mixture was stirred for 12 h. The solvent was evaporated and the residue was purified by flash chromatography (hexanes-EtOAc 15:1) to afford 5b (75 mg, 82%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ6.99 (s, 1H), 5.12 (d, J=16.5, 1H), 5.00 (d, J=16.5, 1H), 4.75 (t, J=6.0 Hz, 1H), 2.33-2.31 (m, 1H), 2.07-1.99 (m, 2H) 2.06 (s, 3H), 1.84-1.60 (m, 2H), 1.00 (s, 14H), 0.88 (t, J=7.4 Hz, 3H), 0.83-0.79 (m, 2H); 13C NMR (75 MHz, CDCl3) δ162.4, 152.5, 123.7, 118.6, 94.2, 72.8, 71.5, 44.3, 31.1, 25.3, 17.5, 12.6, 9.4, 0.3.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by flash chromatography (hexanes-EtOAc 15:1)

Sources & evidence

ORD record
ord-8fc7d8718346437bb4a5ce56c6cb3a8f
Source dataset
uspto-grants-2004_06
Patent number
US06749756B1

Reaction notes

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