Cesium carbonate → HCID 77454430, compound

HRID 573736Notes

Reaction equation

HRID 573736 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:18][C:17]2([CH2:21][CH2:20][CH2:19]2)[CH2:16][C:15]2[N:14]=[C:13]([CH:22]([CH3:24])[CH3:23])[C:12]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:11](I)[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[O:31]1[CH2:36][CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH2:33][CH2:32]1.C(=O)([O-])[O-].[Cs+].[Cs+].[F-].[Cs+]>O.O1CCCC1.C1(C)C=CC=CC=1>[Si:1]([O:8][CH:9]1[CH2:18][C:17]2([CH2:21][CH2:20][CH2:19]2)[CH2:16][C:15]2[N:14]=[C:13]([CH:22]([CH3:24])[CH3:23])[C:12]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:11]([C:34]3[CH2:35][CH2:36][O:31][CH2:32][CH:33]=3)[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 25953Cesium fluorideHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 68061449HCID 68061449, compound

Product 1

HCID 77454430HCID 77454430, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22635083Tetrahydrofuran tolueneSolvent

Procedure

Obtained by starting from (S)-ethyl 5′-(tert-butyldimethylsilyloxy)-4′-iodo-2′-isopropyl-6′,8′-dihydro-5′H-spiro[cyclobutane-1,7′-quinoline]-3′-carboxylate 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 4:1.

Workup

  1. customObtained

Sources & evidence

ORD record
ord-f2092280da4d40b08fafac1049560378
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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