Potassium Carbonate → Ethyl 6'-bromo-4-methoxy-1'-(2-(trimethylsilyl)ethylsulfonamido)-1',3'-dihydrospiro[cyclohexane-1,2'-indene]-1'-carboxylate

HRID 1503466Notes

Reaction equation

HRID 1503466 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:30][CH2:29][CH:28]([O:31][CH3:32])[CH2:27][CH2:26]3)[C:8]2([NH:16][S:17]([CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])(=[O:19])=[O:18])[C:11]([O:13][CH2:14][CH3:15])=C)=[CH:4][CH:3]=1.C([O-])([O-])=[O:34].[K+].[K+].FC(F)CI>CC#N>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:30][CH2:29][CH:28]([O:31][CH3:32])[CH2:27][CH2:26]3)[C:8]2([NH:16][S:17]([CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])(=[O:18])=[O:19])[C:11]([O:13][CH2:14][CH3:15])=[O:34])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 38335651,1-Difluoro-2-iodoethaneHCID 67043662N-(6'-bromo-1'-(1-ethoxyvinyl)-4-methoxy-1',3'-dihydrospiro[cyclohexane-1,2'-indene]-1'-yl)-2-(trimethylsilyl)ethanesulfonamide

Product 1

HCID 67043624Ethyl 6'-bromo-4-methoxy-1'-(2-(trimethylsilyl)ethylsulfonamido)-1',3'-dihydrospiro[cyclohexane-1,2'-indene]-1'-carboxylateYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of compound 9 (100 mg, 0.27 mmol) in CH3CN (5 mL) was added K2CO3 (74 mg, 0.54 mmol). After addition, the resulting mixture was stirred at room temperature for 10 min. Then 1,1-difluoro-2-iodo-ethane (51.8 mg, 0.27 mmol) in CH3CN (5 mL) was added dropwise via a syringe with stirring. The mixture was stirred at 60° C. overnight. Then the mixture was filtered off, the filtrate was concentrated to give compound 10 (90 mg, 77%) as a white solid, which was used for the next step directly without purification. LC-MS tR=1.337 min in 2 min chromatography, MS (ESI) m/z 435.2 [M+H]+.

Workup

  1. additionAfter addition
  2. stirringwith stirring
  3. stirringThe mixture was stirred at 60° C. overnight
  4. filtrationThen the mixture was filtered off
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d9acdacf6e73495b82cb07066c37aab1
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

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