(4-Ethynylphenyl)methanol → HCID 178451390, compound

HRID 1045101Notes

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]([CH2:29][OH:30])=[CH:25][CH:24]=1)#[CH:22]>CN(C=O)C.[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]([CH2:29][OH:30])=[CH:25][CH:24]=3)=[CH:17][C:11]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 120 °C

Procedure

A 2 mL Biotage™ microwave vial 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 (4-ethynyl-phenyl)-methanol (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 used in the next step without further purification. LR-MS (API-ES): calculated for C22H21ClN2O3S 428.1, observed m/e 429.0 (M+H)+ (Rt 3.05 min).

Workup

customThe solvent was removed in vacuo
customto give dark brown oil which
customwas used in the next step without further purification

Sources & evidence

ORD record: ord-0cc11599284f48169d5bd6c5fbf8a528
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563746B2

Reaction notes

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