Cesium fluoride → HCID 117727761, compound

HRID 61203Notes

Reaction equation

HRID 61203 reaction equation
[F:1][C:2]1[C:28]([F:29])=[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:36]1[N:41]=[CH:40][CH:39]=[CH:38][N:37]=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[C:28]([F:29])=[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:36]2[N:41]=[CH:40][CH:39]=[CH:38][N:37]=2)[CH:3]=1

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 27632512-(Tributylstannyl)pyrimidineHCID 117727742HCID 117727742, compound

Product 1

HCID 117727761HCID 117727761, compound

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-(4,5-difluoro-2-iodobenzoyl)-3-methylpiperidin-2-yl)methyl)isoindoline-1,3-dione (0.738 g, 1.409 mmol), 2-(tributylstannyl)pyrimidine (0.52, 1.409 mmol), CsF (0.43 g, 2.818 mmol), CuI (0.027 g, 0.14 mmol) and Pd(PPh3)4 (0.16 g, 0.14 mmol) in DMF (15 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. MS (ESI) 477 (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-7b91adfa66e44da6a9aef824f06c4bd8
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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