Triethylamine → HCID 89718627, compound

HRID 1056865Notes

Reaction equation

HRID 1056865 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH3:12][CH:13]([OH:16])[C:14]#[CH:15].CCN(CC)CC>[Cl-].[Cl-].[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[F:1][C:2]1[CH:10]=[C:6]2[C:5]([CH:15]=[C:14]([CH:13]([OH:16])[CH3:12])[O:9][C:7]2=[O:8])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 162393-Butyn-2-olHCID 131585835-Fluoro-2-iodobenzoic acid

Product 1

HCID 89718627HCID 89718627, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-fluoro-2-iodobenzoic acid (9.04 g, 34.0 mmol), but-3-yn-2-ol (5.7 mL, 5.46 g, 78.0 mmol), ZnCl2 (4.62 g, 34.0 mmol), Pd(Ph3P)4 (1.96 g, 1.7 mmol), Et3N (14.2 mL, 10.3 g, 102.0 mmol) and DMF (50 mL) was stirred under argon at 100° C. for 2 hours. After the removal of the volatiles under vacuum, the residue was chromatographed (silica gel, ethyl acetate in hexanes, 0-50%) to provide intermediate 7-fluoro-3-(1-hydroxyethyl)-1H-isochromen-1-one as a brown oil (5.93 g, 84%). MS m/z 209.2 [M+H]+; 1H NMR (500 MHz, CDCl3-d): 6 ppm 7.91-7.96 (1H, m), 7.43-7.47 (2H, m), 6.55-6.59 (1H, m), 4.67 (1H, q, J=6.52 Hz), 1.57 (3H, d, J=6.62 Hz).

Workup

  1. customAfter the removal of the volatiles under vacuum
  2. customthe residue was chromatographed (silica gel, ethyl acetate in hexanes, 0-50%)

Sources & evidence

ORD record
ord-8344ab6621e64c12aa495df6e190ff04
Source dataset
uspto-grants-2016_07
Patent number
US09399649B2

Reaction notes

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