Cesium carbonate → HCID 66762289, compound

HRID 573728Notes

Reaction equation

HRID 573728 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]2[N:14]=[C:13]([CH:21]([CH3:23])[CH3:22])[C:12]([CH2:24][OH:25])=[C:11](I)[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[O:27]1[CH2:32][CH:31]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH2:29][CH2:28]1.[C:42](=[O:45])([O-])[O-].[Cs+].[Cs+].[F-].[Cs+]>O.O1CCCC1.C1(C)C=CC=CC=1>[C:4]([O:45][C:42]1[CH:17]=[CH:18][C:9]([C@H:24]([C:12]2[C:13]([CH:21]([CH3:23])[CH3:22])=[N:14][C:15]3[CH2:16][C:17]([CH3:20])([CH3:19])[CH2:18][C@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[C:10]=3[C:11]=2[C:30]2[CH2:29][CH2:28][O:27][CH2:32][CH:31]=2)[OH:25])=[CH:10][CH:15]=1)([CH3:7])([CH3:6])[CH3:5]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 25953Cesium fluorideHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 66762027HCID 66762027, compound

Product 1

HCID 66762289HCID 66762289, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22635083Tetrahydrofuran tolueneSolvent

Procedure

Obtained by starting from (R)-(4-tert-butoxyphenyl)((S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-3-ylmethanol and 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. A 2 M solution of caesium carbonate in water is used instead caesium fluoride. The reaction is run in tetrahydrofurane/toluene 5:1.

Workup

  1. customObtained

Sources & evidence

ORD record
ord-acc0833256c04914a71acf581fa3f711
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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