HCID 67099310, compound → HCID 67099651, compound

HRID 2078132Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[C:7](=[O:14])[C:6]([C:15]([NH:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:16])=[C:5]2[OH:26].[Cu](C#N)[C:28]#[N:29]>[C-]#N.C([N+](CC)(CC)CC)C.O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:28]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[C:7](=[O:14])[C:6]([C:15]([NH:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:16])=[C:5]2[OH:26])#[N:29]

Participants

Conditions

Temperature: 75 °C

Procedure

1,1-Dimethylethyl N-((6-bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-yl)carbonyl)glycinate (297 mg, 700 μmol, prepared in Example 40A-D), dppf (155 mg, 280 μmol), tris(dibenzylideneacetone)dipalladium (64.1 mg, 70.0 μmol), copper cyanide (251 mg, 2800 μmol), and tetraethylammonium cyanide (120 mg, 770 μmol) were mixed in dioxane (6 mL) in a microwave tube under a nitrogen atmosphere. The reaction mixture was then stirred at 75° C. for 5.5 hours. The reaction mixture was returned to room temperature, fused to silica gel, and purified by silica flash chromatography (0-100% DCM/hexane) to give the desired ester as an off-white solid (127 mg). MS (m/e)=315.1 (M+H-tBu)+.

Workup

customwas returned to room temperature
custompurified by silica flash chromatography (0-100% DCM/hexane)

Sources & evidence

ORD record: ord-419638cb08874da99e3938fcbb56bb4c
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928139B2

Reaction notes

Loading…