1-Ethynyl-4-phenoxybenzene → HCID 178451391, compound

HRID 1045103Notes

Reaction equation

HRID 1045103 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][S:8][C:9]1[NH:13][C:12]2[CH:14]=[C:15]([Cl:19])[C:16](I)=[CH:17][C:11]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2].[C:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:25][CH:24]=1)#[CH:22]>CN(C=O)C.CO.CCOC(C)=O.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:5][C:6](=[O:20])[CH2:7][S:8][C:9]1[NH:13][C:12]2[CH:14]=[C:15]([Cl:19])[C:16]([C:22]#[C:21][C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:25][CH:24]=3)=[CH:17][C:11]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 2

HCID 127880241-Ethynyl-4-phenoxybenzeneHCID 58387110Tert-butyl 2-(6-chloro-5-iodo-1H-benzo[d]imidazol-2-ylthio)acetate2×

Product 1

HCID 178451391HCID 178451391, compound

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent2×HCID 21584119Ethylacetate methanolSolvent

Conditions

Temperature
120 °C

Procedure

A 2 mL Biotage™ microwave vial equipped with a stirring bar was charged with copper iodide (1.1 mg, 10 mol %), and Pd(PPh3)2Cl2 (2.1 mg, 5 mol %). A solution of (6-chloro-5-iodo-1H-benzoimidazol-2-ylsulfanyl)-acetic acid tert-butyl ester (Intermediate 4, 25.0 mg, 0.059 mmol) in DMF (0.5 mL) was added to the vial, followed by a solution of 1-ethynyl-4-phenoxy-benzene (15.0 mg, 0.118 mmol) in DMF (250 uL) and TEA (57 uL, 0.41 mmol). The resulting suspension was heated in a microwave synthesizer (Biotage Initiator™) at 120° C. for 5 min. The solvent was removed in vacuo to give dark brown oil which was re-dissolved in a 1:1 MeOH/EtOAc mixture (3 mL) and passed through a Thiol StratoSphere™ SPE cartridge (Polymer Labs). The resulting solution was evaporated to dryness in vacuo to give the crude product as brown solid. LR-MS (API-ES): calculated for C27H23ClN2O3S 490.1, observed m/e 491.0 (M+H)+ (Rt 3.74 min). The crude product was used in the next step without further purification.

Workup

  1. customA 2 mL Biotage™ microwave vial equipped with a stirring bar
  2. customThe solvent was removed in vacuo
  3. customto give dark brown oil which
  4. customThe resulting solution was evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-3def5c6e62b34a98af29897033c6ee11
Source dataset
uspto-grants-2013_10
Patent number
US08563746B2

Reaction notes

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