Potassium Carbonate → HCID 23508107, compound

HRID 1883608Notes

Reaction equation

HRID 1883608 reaction equation
B1([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)C2CCCC1CCC2.Br[C:18]1[C:23]2[O:24][CH:25]3[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH:26]3[C:22]=2[CH:21]=[C:20]([C:38]2[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][C:39]=2[Cl:45])[CH:19]=1.C([O-])([O-])=O.[K+].[K+]>O>[CH2:10]([C:18]1[C:23]2[O:24][CH:25]3[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:36])([CH3:37])[CH3:35])=[O:32])[CH2:27][CH:26]3[C:22]=2[CH:21]=[C:20]([C:38]2[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][C:39]=2[Cl:45])[CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 41509249-Benzyl-9-borabicyclo(3.3.1)nonaneHCID 23508114HCID 23508114, compound

Product 1

HCID 23508107HCID 23508107, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

B-Benzyl-9-BBN (1.3 mL 0.5 M sol in THF, 0.650 mmol) was added to degassed DMF (3 mL), followed by sequential addition of tert-butyl 6-bromo-8-(2,4-dichlorophenyl)-3,4,4a,9b-tetrahydro[1]benzofuro[3,2-c]pyridine-2(1H)-carboxylate (0.255 g, 0.511 mmol), catalyst Cl2PdDPPF (0.018 g, 0.022 mmol) and K2CO3 (0.220 g, 1.592 mmol). The reaction mixture was stirred under N2 at 65° C. for 6 h. The reaction mixture was poured into water and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude was purified by chromatography (14% EtOAc/Hexane) and tert-butyl 6-benzyl-8-(2,4-dichlorophenyl)-3,4,4a,9b-tetrahydro[1]benzofuro[3,2-c]pyridine-2(1H)-carboxylate was obtained in 77% yield (0.200 g, 0.392 mmol). MS (ESI+) for C29H29Cl2NO3 m/z 510.1 (M+H)+.

Workup

  1. customto degassed DMF (3 mL)
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified by chromatography (14% EtOAc/Hexane)

Sources & evidence

ORD record
ord-f4f9246a032b42298982222f8183120c
Source dataset
uspto-grants-2004_07
Patent number
US06762191B2

Reaction notes

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