Water → tert-butyl N-[5-methylsulfanyl-4-[3-[5-methyl-1-(2-trimethylsilylethoxymethyl)benzimidazol-4-yl]phenyl]sulfonylthiophene-2-carboximidoyl]carbamate

HRID 723237Notes

Reaction equation

HRID 723237 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]([C:10]1[S:11][C:12]([S:27][CH3:28])=[C:13]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20](B(O)O)[CH:19]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2].I[C:31]1[C:39]2[N:38]=[CH:37][N:36]([CH2:40][O:41][CH2:42][CH2:43][Si:44]([CH3:47])([CH3:46])[CH3:45])[C:35]=2[CH:34]=[CH:33][C:32]=1[CH3:48].C([O-])([O-])=O.[Na+].[Na+].C1(C)C=CC=CC=1.O>CCO.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>[C:1]([O:5][C:6](=[O:29])[NH:7][C:8](=[NH:9])[C:10]1[S:11][C:12]([S:27][CH3:28])=[C:13]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:31]3[C:39]4[N:38]=[CH:37][N:36]([CH2:40][O:41][CH2:42][CH2:43][Si:44]([CH3:47])([CH3:46])[CH3:45])[C:35]=4[CH:34]=[CH:33][C:32]=3[CH3:48])[CH:19]=2)(=[O:17])=[O:16])[CH:14]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 218867434-Iodo-5-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazoleHCID 68544146Na2CO3 tolueneHCID 140043492[3-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonylphenyl]boronic acid

Product 1

HCID 145857650tert-butyl N-[5-methylsulfanyl-4-[3-[5-methyl-1-(2-trimethylsilylethoxymethyl)benzimidazol-4-yl]phenyl]sulfonylthiophene-2-carboximidoyl]carbamateYield 71%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of {[4-(3-dihydroxyboranyl-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester. (20 mg, 0.044 mmol, Example 140: step a), 4-Iodo-5-methyl-1-(2-methylsilanyl-ethoxymethyl)-1H-benzoimidazole (21 mg, 0.054 mmol, Example 287: step b) and Pd(PPh3)4 in 1.2 ml of 1:1:2 EtOH/2M Na2CO3/toluene was stirred at 90° C. for 5 h, the cooled to RT. Treated with 3 mL of H2O, the mixture was extracted with EtOAc (3×5 mL)/Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (30% EtOAc/hexane) gave 21 mg (71%) of product as a light yellow solid: 1H-NMR (CDCl3; 400 MHz) δ 8.42 (s, 1H). 8.08 (s, 1H), 8.05 (s, 1H), 8.01 (ddd, 1H, J=7.2, 1.8, 1.7 Hz), 7.71–7.67 (m, 2H), 7.57 (d, 1H, J=8.4 Hz), 7.39 (d, 1H, J=8.7 Hz), 5.64 (s, 2H), 3.57 (t, 2H, J=8.3 Hz), 2.61 (s, 3H), 2.33 (s, 3H), 1.51 (s, 9H), 0.95 (t, 2H, J=8.3), −0.03 (s, 9H). Mass spectrum (ESI, m/z): Calcd. for C31H40N4O5S3Si, 673.2, (M+H), found 672.9.

Workup

  1. extractionthe mixture was extracted with EtOAc (
  2. custom3×5 mL)/Removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-8a15fc2a0dae40b9af32c6bc6add4698
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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