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Cesium fluoride → 5-(3-(6-chloropyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine

HRID 634141
Notes
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Reaction equation

HRID 634141 reaction equation
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[S:15][C:14]([NH:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=4)=[N:13][N:12]=3)[CH:9]=2)[N:4]([S:26]([C:29]2[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=2)(=[O:28])=[O:27])[CH:3]=1.[Cl:36][C:37]1[CH:42]=[N:41][CH:40]=[C:39]([Sn](CCCC)(CCCC)CCCC)[N:38]=1.[F-].[Cs+]>CN(C=O)C.C(Cl)Cl.[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:36][C:37]1[N:38]=[C:39]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:11]4[S:15][C:14]([NH:16][CH2:17][C:18]5[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=5)=[N:13][N:12]=4)[CH:9]=3)[N:4]([S:26]([C:29]3[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=3)(=[O:28])=[O:27])[CH:3]=2)[CH:40]=[N:41][CH:42]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 25953Cesium fluorideHCID 117740572-Chloro-6-(tributylstannyl)pyrazineHCID 683285925-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine

Product 1

HCID 867250965-(3-(6-chloropyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amineYield 68.2%

Reagents, catalysts & solvents 4

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 178418397HCID 178418397, compoundCatalyst
HCID 6228DimethylformamideSolvent
HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A glass microwave reaction vessel was charged with 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine (1.50 g, 2.433 mmol) and 2-chloro-6-(tributylstannyl)pyrazine (1.473 g, 3.65 mmol) in DMF (20 mL) followed by cesium fluoride (555 mg, 3.65 mmol), CuI (46 mg, 0.243 mmol) and Pd(PPh3)4 (0.281 g, 0.243 mmol). The reaction was stirred and heated in a Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 100° C. for 1 h, then the mixture was diluted with DCM and washed with H2O. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified silica gel chromatography (eluting with 20-60% EtOAc in Hex) to give 5-(3-(6-chloropyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine (1.0 g, 68.2%) as a solid. MS (ESI, pos. ion) m/z: 603 (M+1).

Workup

  1. customA glass microwave reaction vessel
  2. washwashed with H2O
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified
  7. washsilica gel chromatography (eluting with 20-60% EtOAc in Hex)

Sources & evidence

ORD record
ord-05900c8d1fb5402881928ce558738ea6
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09321756B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes