Borohydride → HCID 11387669, compound

HRID 1171448Notes

Reaction equation

HRID 1171448 reaction equation
[BH4-].[CH2:2]([C:9]1[N:10]([CH3:15])[C:11]([SH:14])=[N:12][N:13]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH3:16][O:17][C:18](=[O:43])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31](I)=[CH:30][C:29]=2[O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])=[CH:22][CH:21]=1>O1CCCC1.C(O)C>[CH3:16][O:17][C:18](=[O:43])[CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([S:14][C:11]3[N:10]([CH3:15])[C:9]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[N:13][N:12]=3)=[CH:30][C:29]=2[O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 28123BorohydrideHCID 68768207HCID 68768207, compoundHCID 178442555HCID 178442555, compound

Product 1

HCID 11387669HCID 11387669, compound

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent2×

Procedure

979 mg (2.45 mmol, 3 eq) of resin-supported borohydride and 11 mg (0.02 mmol, 0.03 eq) of bis(bipyridine)dibromonickel (II) are added to a solution of 244 mg (1.22 mmol, 1.5 eq) of 5-heptyl-4-methyl-4H-[1,2,4]-triazole-3-thiol in 4 ml of tetrahydrofuran/ethanol 5/5. To the suspension obtained there is added a solution of 405 mg (0.82 mmol, 1 eq) of [4-(2-heptyloxy-4-iodobenzyloxy)phenyl]acetic acid methyl ester in 4 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. The residue is chromatographed on silica gel (heptane/ethyl acetate: gradient from 70/30 to 50/50). After concentration, 427 mg (92%) of the expected compound are obtained.

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. customThe residue is chromatographed on silica gel (heptane/ethyl acetate: gradient from 70/30 to 50/50)
  7. concentrationAfter concentration, 427 mg (92%) of the expected compound
  8. customare obtained

Sources & evidence

ORD record
ord-27e74181da3847a1a47edaccc388c87b
Source dataset
uspto-grants-2010_11
Patent number
US07829588B2

Reaction notes

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