HCID 57577469, compound → HCID 67538393, compound

HRID 2241006Notes

Reaction equation

HRID 2241006 reaction equation
[F:1][CH:2]([F:14])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]#[CH:13])[CH:7]=1.[F:15][CH:16]([F:26])[O:17][C:18]1[CH:23]=[CH:22][C:21](I)=[CH:20][C:19]=1[CH3:25]>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.CN(C=O)C>[F:15][CH:16]([F:26])[O:17][C:18]1[CH:23]=[CH:22][C:21]([C:13]#[C:12][C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([O:5][CH2:4][CH2:3][CH:2]([F:14])[F:1])[CH:7]=2)=[CH:20][C:19]=1[CH3:25]

Participants

6

Reactant 2

HCID 57577469HCID 57577469, compoundHCID 86627697HCID 86627697, compound

Product 1

HCID 67538393HCID 67538393, compound

Reagents, catalysts & solvents 3

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

Procedure

This compound was made in a similar manner to Example 89 Step 4 using 1-(3,3-difluoropropoxy)-3-ethynylbenzene (650 mg, 3.13 mmol) from the previous step, 1-(difluoromethoxy)-4-iodo-2-methylbenzene (818 mg, 2.88 mmol), TEA (1.45 g, 2.0 mL, 14.5 mmol), PdCl2(PPh3)2 (101 mg, 0.144 mmol), and CuI (16.4 mg, 0.0864 mmol), and DMF (4.4 mL) to provide the title compound as a yellow oil.

Sources & evidence

ORD record
ord-5c0ef3d4bbd64421b54da4d32f796850
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

Loading…