Cesium carbonate → HCID 66762588, compound

HRID 573713Notes

Reaction equation

HRID 573713 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]([CH:24]=[O:25])=[C:11]([I:26])[C:10]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].I[C:28]1[CH:33]=[CH:32][C:31]([O:34][CH:35]([CH3:37])[CH3:36])=[CH:30][CH:29]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F-].[Cs+].C([Mg]Cl)(C)C.[Cl-].[Li+].C([Mg]Cl)(C)C>O.O1CCCC1>[Si:1]([O:8][C@H:9]1[CH2:18][C:17]([CH3:19])([CH3:20])[CH2:16][C:15]2[N:14]=[C:13]([CH:21]([CH3:22])[CH3:23])[C:12]([C@H:24]([C:28]3[CH:33]=[CH:32][C:31]([O:34][CH:35]([CH3:37])[CH3:36])=[CH:30][CH:29]=3)[OH:25])=[C:11]([I:26])[C:10]1=2)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

9

Reactant 6

HCID 10796Cesium carbonateHCID 25953Cesium fluorideHCID 147851721-Iodo-4-isopropoxy-benzeneHCID 86662512(S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinoline-3-carbaldehydeHCID 178418918HCID 178418918, compoundHCID 178461733HCID 178461733, compound

Product 1

HCID 66762588HCID 66762588, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Obtained by starting from (S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinoline-3-carbaldehyde and 1-iodo-4-isopropoxybenzene. A 2 M solution of caesium carbonate in water is used instead caesium fluoride. A 1.3 M solution of isopropylmagnesium chloride-lithium chloride-complex in tetrahydrofurane is used instead of a 2 M solution of isopropylmagnesium chloride in tetrahydrofurane.

Workup

  1. customObtained

Sources & evidence

ORD record
ord-641f0fb2e99e4e129ae110a5013a913a
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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