Cesium fluoride → HCID 23508126, compound

HRID 1883610Notes

Reaction equation

HRID 1883610 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]([S:29][Si](C(C)C)(C(C)C)C(C)C)[C:12]2[O:21][CH:20]3[CH:15]([CH2:16][N:17]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:19]3)[C:13]=2[CH:14]=1.I[CH2:41][CH2:42][CH3:43].[F-].[Cs+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]([S:29][CH2:41][CH2:42][CH3:43])[C:12]2[O:21][CH:20]3[CH:15]([CH2:16][N:17]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[CH2:18][CH2:19]3)[C:13]=2[CH:14]=1

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 336431-IodopropaneHCID 23508106HCID 23508106, compound

Product 1

HCID 23508126HCID 23508126, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl 8-(2,4-dichlorophenyl)-6-[(triisopropylsilyl)thio]-3,4,4a,9b-tetrahydro[1]benzofuro[3,2-c]pyridine-2(1H)-carboxylate (0.111 g, 0.182 mmol) was dissolved in DMF (3 mL). 1-Iodopropane (0.2 mL) and cesium fluoride (0.060 g) were added to the reaction mixture. The reaction mixture was stirred at rt under N2 for 2.5 h. The reaction mixture was partitioned between EtOAc (30 mL) and 2:3 water:brine (25 mL). The aqueous layer was back extracted with EtOAc (30 mL). The combined organic layers were washed with water (20 mL), with brine (20 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. tert-Butyl 8-(2,4-dichlorophenyl)-6-(propylthio)-3,4,4a,9b-tetrahydro[1]benzofuro[3,2-c]pyridine-2(1H)-carboxylate was obtained in quantitative yield (0.090 g). MS (ESI+) for C25H29Cl2NO3S m/z 517.0 (M+23)+.

Workup

  1. customThe reaction mixture was partitioned between EtOAc (30 mL) and 2:3 water
  2. extractionThe aqueous layer was back extracted with EtOAc (30 mL)
  3. washThe combined organic layers were washed with water (20 mL), with brine (20 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0ebebfb963184c4f800bd7b1386c5b29
Source dataset
uspto-grants-2004_07
Patent number
US06762191B2

Reaction notes

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