Cesium carbonate → HCID 66715935, compound

HRID 2271600Notes

Reaction equation

HRID 2271600 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([CH:14]1[CH2:16][CH2:15]1)=[O:13])=[C:5]2[Cl:17].C([O-])([O-])=O.[Cs+].[Cs+].[Cl:24][C:25]1[CH:30]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:28]=[C:27]([O:40][CH3:41])[C:26]=1[OH:42]>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.Cl[Pd]Cl.[Fe+2]>[Cl:17][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:29]3[CH:28]=[C:27]([O:40][CH3:41])[C:26]([OH:42])=[C:25]([Cl:24])[CH:30]=3)[CH:3]=2)[N:8]=[CH:7][C:6]=1[C:12]([CH:14]1[CH2:16][CH2:15]1)=[O:13]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 177502302-Chloro-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 66715111(6-Bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone

Product 1

HCID 66715935HCID 66715935, compoundYield 16.9%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

To a suspension of (6-bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone (104 mg, 0.320 mmol), Pd(dppf)Cl2 (23 mg, 0.03 mmol), and Cs2CO3 (0.95 mL, 1.0 M in H2O) in dioxane (5 mL) was added 2-chloro-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (109 mg, 0.384 mmol). The reaction mixture was degassed with N2 gas and the vessel was sealed and heated to 40° C. for 18 h. The reaction mixture was cooled, diluted with ethyl acetate, and filtered. The solution was concentrated and subjected to column chromatography (silica, hexanes/ethyl acetate) to afford the desired product (21 mg, 13%) as a light brown solid: 1H NMR (300 MHz, CDCl3) δ 8.91 (s, 1H), 8.43 (d, J=1.9 Hz, 1H), 8.19 (t, J=7.5 Hz, 1H), 8.10-7.91 (m, 1H), 7.36 (d, J=1.9 Hz, 1H), 7.13 (d, J=1.8 Hz, 1H), 6.03 (s, 1H), 4.04 (s, 3H), 2.77-2.50 (m, 1H), 1.50-1.37 (m, 2H), 1.35-1.10 (m, 2H).

Workup

  1. customThe reaction mixture was degassed with N2 gas
  2. customthe vessel was sealed
  3. temperatureThe reaction mixture was cooled
  4. additiondiluted with ethyl acetate
  5. filtrationfiltered
  6. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-efadb05e0b5f48e4ab6d9741e722e6bb
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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