Cesium fluoride → HCID 67265010, compound

HRID 1685099Notes

Reaction equation

HRID 1685099 reaction equation
[NH2:1][C:2]1[C:6](Br)=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[S:4][C:3]=1[C:14]([O:16][CH3:17])=[O:15].CC1(C)C(C)(C)OB([C:26]2[CH:27]=[C:28]3[C:32](=[CH:33][CH:34]=2)[NH:31][CH:30]=[CH:29]3)O1.[F-].[Cs+]>COCCOC.CO.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:1][C:2]1[C:6]([C:26]2[CH:27]=[C:28]3[C:32](=[CH:33][CH:34]=2)[NH:31][CH:30]=[CH:29]3)=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[S:4][C:3]=1[C:14]([O:16][CH3:17])=[O:15]

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 27347725-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indoleHCID 67265060HCID 67265060, compound

Product 1

HCID 67265010HCID 67265010, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of EXAMPLE 8A (0.125 g, 0.4 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (0.122 g, 0.5 mmol), tetrakis(triphenylphosphine) palladium(0) (22.4 mg, 0.02 mmol) and cesium fluoride (0.182 g, 1.2 mmol) in 1,2-dimethoxyethane (2 mL) and methanol (1 mL) was heated at 150° C. for 10 minutes under microwave conditions (CEM Discovery). After cooling, the mixture was purified by flash chromatography on silica gel using 3:7 ethyl acetate/hexanes to give 98 mg (71%) of the title compound. 1H NMR (DMSO-d6) δ 11.18 (s, 1H), 7.37-7.43 (m, 3H), 7.17-7.23 (m, 5H), 6.85 (dd, J=8.3, 1.5, 1H), 6.42-6.43 (m, 1H), 5.92 (s, 2H), 3.78 (s, 3H).

Workup

  1. temperatureAfter cooling
  2. customthe mixture was purified by flash chromatography on silica gel using 3:7 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-aae0d5b45aac4b749c3b27f24552ee8e
Source dataset
uspto-grants-2012_04
Patent number
US08148384B2

Reaction notes

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