Potassium Carbonate → HCID 178498872, compound

HRID 1054855Notes

Reaction equation

HRID 1054855 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:11][C@H:10]([OH:12])[CH2:9]2)=[CH:4][CH:3]=1.[Cl:13][C:14]1[CH:22]=[C:21]2[C:17]([C:18]([C:23]([O:25][CH3:26])=[O:24])=[CH:19][NH:20]2)=[CH:16][C:15]=1B1OCC(C)(C)CO1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.C(OCC)(=O)C.O>[Cl:13][C:14]1[CH:22]=[C:21]2[C:17]([C:18]([C:23]([O:25][CH3:26])=[O:24])=[CH:19][NH:20]2)=[CH:16][C:15]=1[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:11][C@H:10]([OH:12])[CH2:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 86698665methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylateHCID 178521619HCID 178521619, compound

Product 1

HCID 178498872HCID 178498872, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolventHCID 21863594Toluene ethanolSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of trans-3-(4-bromophenyl)cyclobutanol (200 mg, 0.88 mmol) in toluene/ethanol (4 mL, v/v=1/1) was added methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate (296 mg, 0.968 mmol), potassium carbonate (360 mg, 2.64 mmol), water (1 mL) and Pd(dppf)C12 (46 mg, 0.06 mmol) under nitrogen. The mixture was stirred at 110° C. for 2 hours. The mixture was diluted with ethyl acetate and water. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried and concentrated. The residue was purified by silica gel combiflash to give the title compound (190 mg, 61%) as a light yellow solid. 1H NMR (500 MHz, CD3OD) δ 8.02 (s, 1 H), 8.01 (s, 1 H), 7.60 (s, 1 H), 7.40-7.35 (m, 4 H), 4.52 (m, 1 H), 3.88 (s, 3 H), 3.66 (m, 1 H), 2.57-2.44 (m, 4 H).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel combiflash

Sources & evidence

ORD record
ord-50bdafd790204dc1a10a50f76c260721
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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