Sodium Hydroxide → HCID 46898224, compound

HRID 602797Notes

Reaction equation

HRID 602797 reaction equation
Br[C:2]1[CH:3]=[C:4]([S:8]([C:11]([F:31])([C:25]2[O:26][C:27]([CH3:30])=[N:28][N:29]=2)[CH:12]2[CH2:24][C:15]3[NH:16][C:17]4[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][C:22]=4[C:14]=3[CH2:13]2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH3:32][CH2:33]N(C(C)C)C(C)C.C([Si](C)(C)C)#C.[OH-].[Na+]>CN(C=O)C.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:23][C:20]1[CH:19]=[CH:18][C:17]2[NH:16][C:15]3[CH2:24][CH:12]([C:11]([S:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([C:32]#[CH:33])[CH:3]=4)(=[O:10])=[O:9])([F:31])[C:25]4[O:26][C:27]([CH3:30])=[N:28][N:29]=4)[CH2:13][C:14]=3[C:22]=2[CH:21]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 66111TrimethylsilylacetyleneHCID 81531DiisopropylethylamineHCID 46898363HCID 46898363, compound

Product 1

HCID 46898224HCID 46898224, compoundYield 52.8%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 76 mg (0.133 mmol) of (RS, SR)-2-[(3-bromo-benzenesulfonyl)-fluoro-(5-methyl-[1,3,4]oxadiazol-2-yl)-methyl]-7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indole (example 106) in 1.5 mL of DMF was treated with 1 mg (0.005 mmol) of CuI, 37 mg (0.29 mmol) of DIPEA, 17 mg (0.015 mmol) of tetrakis(triphenylphosphine)palladium and 71 mg (0.72 mmol) of ethynyltrimethylsilane and the resulting suspension stirred at 80° C. during 4 hrs. Diluted aqueous NaOH was added and the mixture extracted twice with dichloromethane. The combined organic layers were dried over Na2SO4, filtered and evaporated. Chromatography on silica gel with heptane/EtOAc (1:1) gave 33 mg (48%) of (RS, SR)-7-chloro-2-[(3-ethynyl-benzenesulfonyl)-fluoro-(5-methyl-[1,3,4]oxadiazol-2-yl)-methyl]-1,2,3,4-tetrahydro-cyclopenta[b]indole as a yellow solid, MS: 471 (MH+).

Workup

  1. extractionthe mixture extracted twice with dichloromethane
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-9ddc940d4f774aff820ac6725d4ed34f
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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