Cesium fluoride → HCID 86710226, compound

HRID 2405907Notes

Reaction equation

I[C:2]1[CH:3]=[N:4][N:5]([CH2:7][CH2:8][C@@:9]([CH3:19])([S:15]([CH3:18])(=[O:17])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=1.[C:20]1(B(O)O)[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]=1.[F-].[Cs+]>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.C1COCC1>[C:20]1([C:2]2[CH:3]=[N:4][N:5]([CH2:7][CH2:8][C@@:9]([CH3:19])([S:15]([CH3:18])(=[O:17])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a vial containing ethyl (2R)-4-(4-iodo-1H-pyrazol-1-yl)-2-methyl-2-(methylsulfonyl)butanoate (500 mg, 1.25 mmol, 1.0 eq), cyclohex-1-en-1-ylboronic acid (205 mg, 1.62 mmol, 1.3 eq), cesium fluoride (759 mg, 5.00 mmol, 4 eq) and Pd(PPh3)4 (100 mg 0.087 mmol, 0.07 eq) was added THF (5 mL). The vial was sealed and the mixture was heated at 60° C. overnight. The mixture was filtered through celite, and eluted with EtOAc. The filtrate was absorbed onto silica gel and purified by flash chromatography, eluting with 0-20% EtOAc/Hpt then 5% MeOH/EtOAc to give ethyl (2R)-4-[4-(cyclohex-1-en-1-yl)-1H-pyrazol-1-yl]-2-methyl-2-(methylsulfonyl)butanoate (370 mg, 83.6% yield). LC-MS M+H+355.1.

Workup

customThe vial was sealed
filtrationThe mixture was filtered through celite
washeluted with EtOAc
customThe filtrate was absorbed onto silica gel
custompurified by flash chromatography
washeluting with 0-20% EtOAc/Hpt then 5% MeOH/EtOAc

Sources & evidence

ORD record: ord-a7b504c17572471da58e3b3a8a5adf1b
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809333B2

Reaction notes

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