Potassium Phosphate, Tribasic → HCID 86691534, compound

HRID 514015Notes

Reaction equation

HRID 514015 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:21]([CH3:22])=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1Cl)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[CH3:24][C:25]1([CH3:40])[CH2:30][CH2:29][C:28](B2OC(C)(C)C(C)(C)O2)=[CH:27][CH2:26]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCCC1.[Cl-].C(N)CC1C=CC=CC=1.[Pd+2].[Cl-]>[C:1]([O:5][C@@H:6]([C:12]1[C:21]([CH3:22])=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[C:28]1[CH2:29][CH2:30][C:25]([CH3:40])([CH3:24])[CH2:26][CH:27]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 231420132-(4,4-Dimethylcyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 68085812(S)-ethyl 2-tert-butoxy-2-(1-chloro-3-methylnaphthalen-2-yl)acetate

Product 1

HCID 86691534HCID 86691534, compoundYield 40.1%

Reagents, catalysts & solvents 2

HCID 86691535HCID 86691535, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of (S)-ethyl 2-tert-butoxy-2-(1-chloro-3-methylnaphthalen-2-yl)acetate (74 mg, 0.22 mmol) and 2-(4,4-dimethylcyclohex-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (78 mg, 0.33 mmol) in tetrahydrofuran (2 mL) was added potassium phosphate (153 mg, 0.66 mmol) and (2-dicyclohexyl-phosphino-2′,6′-dimethoxy-1,1′-biphenyl)[2-(2-aminoethylphenyl)]palladium(II) chloride methyl-t-butyl ether adduct, (SPhos) palladium(II) phenethylamine chloride (15 mg, 0.022 mmol) and the reaction was degassed 10 minutes with argon. The reaction was heated to 110° C. for 1 hour in a microwave reactor. The crude reaction was absorbed onto silica and purified by flash column chromatography (silica gel, ethyl acetate/hexanes) to give a clear white oil (36 mg). 1H-NMR: 400 MHz, (CDCl3) δ: 7.83-7.78 (m, 1H), 7.70 (d, J=7.6 Hz, 1H), 7.53 (s, 1H), 7.43-7.36 (m, 2H), 5.66-5.61 (m, 2H), 4.20-4.03 (m, 2H), 2.66-2.60 (m, 2H), 2.26-2.03 (m, 4H), 1.87-1.59 (m, 5H), 1.24-1.20 (m, 9H), 1.19-1.11 (m, 6H).

Workup

  1. customthe reaction was degassed 10 minutes with argon
  2. customThe crude reaction
  3. customwas absorbed onto silica
  4. custompurified by flash column chromatography (silica gel, ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-0342a6e6850f4ab69ec2d02b9cf9f67b
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

Loading…