Potassium Fluoride → HCID 71212594, compound

HRID 513210Notes

Reaction equation

HRID 513210 reaction equation
Cl[C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:10]([CH2:11][CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=3)=[C:9]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:8](C(OC(C)(C)C)=O)[C:7]=12.[CH2:37]([O:39][C:40]1[CH:41]=[C:42](B(O)O)[CH:43]=[CH:44][CH:45]=1)[CH3:38].[F-].[K+]>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.O1CCOCC1>[CH2:37]([O:39][C:40]1[CH:41]=[C:42]([C:2]2[N:3]=[CH:4][CH:5]=[C:6]3[C:10]([CH2:11][CH2:12][O:13][C:14]4[CH:19]=[CH:18][C:17]([O:20][C:21]([F:23])([F:22])[F:24])=[CH:16][CH:15]=4)=[C:9]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[NH:8][C:7]=23)[CH:43]=[CH:44][CH:45]=1)[CH3:38]

Participants

6

Reactant 3

HCID 522689Potassium Fluoride2×HCID 27739203-Ethoxybenzeneboronic acid2×HCID 86720579HCID 86720579, compound

Product 1

HCID 71212594HCID 71212594, compoundYield 91.5%

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalyst2×HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 1-tert-butyl 2-ethyl 7-chloro-3-{2-[4-(trifluoromethoxy)phenoxy]ethyl}-1H-pyrrolo[2,3-c]pyridine-1,2-dicarboxylate (88 mg, 0.17 mmol), 3-ethoxyphenylboronic acid (69 mg, 0.42 mmol), KF (38.7 mg, 0.67 mmol), and bis(tri-t-butylphosphine)palladium (0) (8.50 mg, 0.02 mmol) was added dioxane (3.5 mL) under a nitrogen atmosphere. The reaction was then heated to 100 C overnight. Another charge of 3-ethoxyphenylboronic acid (69 mg, 0.42 mmol), KF (38.7 mg, 0.67 mmol), and bis(tri-t-butylphosphine)palladium (0) (8.50 mg, 0.02 mmol) was then added and stirring was continued for 4 h. The crude reaction mixture was then concentrated in vacuo, and the crude material was purified on silica (gradient elution, 0-50% EtOAc/hexanes) to yield the title product (80 mg) as a mixture with Boc'd material 1-tert-butyl 2-ethyl 7-(3-ethoxyphenyl)-3-{2-[4-(trifluoromethoxy)phenoxy]ethyl}-1H-pyrrolo[2,3-c]pyridine-1,2-dicarboxylate. HRMS (ESI) calc (M+H)+=515.1788. found 515.1772.

Workup

  1. temperatureThe reaction was then heated to 100 C overnight
  2. additionwas then added
  3. customThe crude reaction mixture
  4. concentrationwas then concentrated in vacuo
  5. customthe crude material was purified on silica (gradient elution, 0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b5d2668a7ccd41978bf98834151114cd
Source dataset
uspto-grants-2015_08
Patent number
US09102673B2

Reaction notes

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