Cesium fluoride → HCID 117727669, compound

HRID 61188Notes

Reaction equation

HRID 61188 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([N:8]2[CH2:13][CH2:12][CH2:11][C@@H:10]([CH3:14])[C@H:9]2[CH2:15][N:16]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:26])=[O:7])=[C:4](I)[CH:3]=1.C([Sn](CCCC)(CCCC)[C:35]1[N:40]=[CH:39][CH:38]=[CH:37][N:36]=1)CCC.[F-].[Cs+]>CN(C=O)C.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([N:8]2[CH2:13][CH2:12][CH2:11][C@@H:10]([CH3:14])[C@H:9]2[CH2:15][N:16]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:26])=[O:7])=[C:4]([C:35]2[N:40]=[CH:39][CH:38]=[CH:37][N:36]=2)[CH:3]=1

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 27632512-(Tributylstannyl)pyrimidineHCID 1177279802-(((2S,3R)-1-(4-Fluoro-2-iodobenzoyl)-3-methylpiperidin-2-yl)methyl)isoindoline-1,3-dione

Product 1

HCID 117727669HCID 117727669, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(((2S,3R)-1-(4-fluoro-2-iodobenzoyl)-3-methylpiperidin-2-yl)methyl)isoindoline-1,3-dione (0.51 g, 1.0 mmol), 2-(tributylstannyl)pyrimidine (0.406 g, 1.1 mmol), CsF (0.304 g, 2.0 mmol), CuI (0.019 g, 0.1 mmol) and Pd(PPh3)4 (0.116 g, 0.1 mmol) in DMF (5 mL) was degassed and heated at 100° C. for 16 h. The solvent was removed in vacuo to obtain the crude which was purified by silica gel chromatography (0˜100% EtOAc/hexanes) to yield the title compound as a white solid (0.370 g, 81%). MS (ESI) 459 (M+H).

Workup

  1. customwas degassed
  2. customThe solvent was removed in vacuo
  3. customto obtain the crude which
  4. customwas purified by silica gel chromatography (0˜100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-dbb5a9bc3bc840fbbadd62c87f3b95fa
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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