Triethylamine → HCID 86712682, compound

HRID 1779034Notes

Reaction equation

HRID 1779034 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:30]=[CH:29][C:16]([CH2:17][N:18]([CH2:26][CH2:27][OH:28])[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:15][CH:14]=2)[N:3]=1.CCN(CC)CC.[C:38]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[CH2:46][C:47]([O:49][CH3:50])=[O:48])#[CH:39].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[C:21]([O:20][C:19]([N:18]([CH2:17][C:16]1[CH:29]=[CH:30][C:13]([NH:12][C:4]2[N:3]=[C:2]([C:39]#[C:38][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=3[CH2:46][C:47]([O:49][CH3:50])=[O:48])[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=2)=[CH:14][CH:15]=1)[CH2:26][CH2:27][OH:28])=[O:25])([CH3:24])([CH3:23])[CH3:22]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 45789861Methyl 2-(2-ethynylphenyl)acetateHCID 86712681HCID 86712681, compound

Product 1

HCID 86712682HCID 86712682, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of tert-butyl 4-((4-chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzyl(2-hydroxyethyl)carbamate (A71) (0.518 g, 1.15 mmol), Et3N (0.75 mL), methyl 2-(2-ethynylphenyl)acetate (K1) (0.242 g, 1.39 mmol), PdCl2(PPh3)2 (0.041 g, 0.058 mmol), CuI (0.022 g, 0.116 mmol) and PPh3 (0.030 g, 0.12 mmol) in DMF (4.5 mL) was heated under microwave irradiation at 120° C. for 15 minutes. The volatiles were evaporated in vacuo and the residue purified using silica gel column chromatography (CombiFlash Rf, 40 g SiO2 cartridge, 20-50% EtOAc in cyclohexane) to give the title compound A72 as an orange foam (0.589 g, 86%); 1H NMR (300 MHz, CDCl3) δ 8.65 (s, 1H), 7.70 (d, J=7.0 Hz, 1H), 7.63 (d, J=8.3 Hz, 2H), 7.48-7.28 (m, 6H), 4.49 (brs, 2H), 3.97 (s, 2H), 3.72 (m, 5H), 3.47 (brs, 2H), 3.01 (brs, 1H), 1.51 (s, 9H). LCMS-B: rt 8.350 min; m/z 585 [M+H]+.

Workup

  1. customThe volatiles were evaporated in vacuo
  2. customthe residue purified

Sources & evidence

ORD record
ord-13a507b5fad743dfa9f2b0bff44df4f6
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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