Borohydride → HCID 11249362, compound

HRID 1171451Notes

Reaction equation

HRID 1171451 reaction equation
[BH4-].[CH3:2][N:3]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[N:6][N:5]=[C:4]1[SH:14].I[C:16]1[CH:35]=[CH:34][C:19]([CH2:20][NH:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:24][CH:23]=2)=[C:18]([O:36][CH2:37][CH2:38][CH3:39])[CH:17]=1>O1CCCC1.C(O)C>[CH2:32]([O:31][C:29](=[O:30])[CH2:28][C:25]1[CH:26]=[CH:27][C:22]([NH:21][CH2:20][C:19]2[CH:34]=[CH:35][C:16]([S:14][C:4]3[N:3]([CH3:2])[C:7]([C:8]4[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=4)=[N:6][N:5]=3)=[CH:17][C:18]=2[O:36][CH2:37][CH2:38][CH3:39])=[CH:23][CH:24]=1)[CH3:33]

Participants

5

Reactant 3

HCID 28123BorohydrideHCID 58828974HCID 58828974, compoundHCID 178481694HCID 178481694, compound

Product 1

HCID 11249362HCID 11249362, compound

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent2×

Procedure

265 mg (0.66 mmol, 3 eq) of resin-supported borohydride and 3 mg (0.01 mmol, 0.03 eq) of bis(bipyridine)dibromonickel (II) are added to a solution of 64 mg (0.33 mmol, 1.5 eq) of 4-methyl-5-pyridin-4-yl-4H-[1,2,4]-triazole-3-thiol in 1.5 ml of tetrahydrofuran/ethanol 5/5. To the suspension obtained there is added a solution of 100 mg (0.22 mmol, 1 eq) of ethyl [4-(4-iodo-2-propoxybenzylamino)phenyl]acetate in 1.5 ml of tetrahydrofuran/ethanol 5/5. The reaction mixture is stirred overnight under reflux. After returning to room temperature, the reaction medium is filtered and then concentrated. 0.111 g (97%) of the expected compound is recovered.

Workup

  1. customTo the suspension obtained there
  2. temperatureunder reflux
  3. customAfter returning to room temperature
  4. filtrationthe reaction medium is filtered
  5. concentrationconcentrated
  6. custom0.111 g (97%) of the expected compound is recovered

Sources & evidence

ORD record
ord-c1fc7246c9064569a3fa767d778b34f0
Source dataset
uspto-grants-2010_11
Patent number
US07829588B2

Reaction notes

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