Bromotrimethylsilane → (5-Chloro-6-phenylethynyl-1H-benzoimidazol-2-ylsulfanylmethyl)-phosphonic acid

HRID 2193853Notes

Reaction equation

HRID 2193853 reaction equation
C([O:3][P:4]([CH2:9][S:10][C:11]1[NH:15][C:14]2[CH:16]=[C:17]([C:21]#[C:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:18]([Cl:20])=[CH:19][C:13]=2[N:12]=1)(=[O:8])[O:5]CC)C.C[Si](Br)(C)C>C(Cl)Cl>[Cl:20][C:18]1[C:17]([C:21]#[C:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:16][C:14]2[NH:15][C:11]([S:10][CH2:9][P:4](=[O:3])([OH:8])[OH:5])=[N:12][C:13]=2[CH:19]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 58422995(5-Chloro-6-phenylethynyl-1H-benzoimidazol-2-ylsulfanylmethyl)-phosphonic acid diethyl ester

Product 1

HCID 58423003(5-Chloro-6-phenylethynyl-1H-benzoimidazol-2-ylsulfanylmethyl)-phosphonic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 1-1 was stirred with TMSBr (0.41 mL, 3.2 mmol) and 2.7 mL of CH2Cl2 for 5 hours before concentrating in vacuo to afford compound 1-2 as an oil. The oil was redissolved in 2 to 3 mL of MeOH and re-concentrated, then triturated with acetonitrile and EtOAc to afford title compound 1-2 as a white powder. mp 210-215° C.; LRMS (API-ES) m/e for C16H12ClN2O3PS (M+H)+, calcd 378.77. found 379.4; Anal. Calcd for C16H12ClN2O3PS+1 HBr: C, 41.81; H, 2.85; N, 6.09. Found: C, 42.11; H, 2.66; N, 6.21.

Workup

  1. concentrationbefore concentrating in vacuo

Sources & evidence

ORD record
ord-05242bb4ed3e460bb2ff92d9a75c0b08
Source dataset
uspto-grants-2012_12
Patent number
US08329914B2

Reaction notes

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